EP4039668A1 - Olefinzusammensetzungen - Google Patents
Olefinzusammensetzungen Download PDFInfo
- Publication number
- EP4039668A1 EP4039668A1 EP21217071.6A EP21217071A EP4039668A1 EP 4039668 A1 EP4039668 A1 EP 4039668A1 EP 21217071 A EP21217071 A EP 21217071A EP 4039668 A1 EP4039668 A1 EP 4039668A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- mol
- alternatively
- group
- monoolefins
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 310
- 150000001336 alkenes Chemical class 0.000 title description 15
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title description 12
- 150000005673 monoalkenes Chemical class 0.000 claims abstract description 251
- 238000000034 method Methods 0.000 claims abstract description 114
- 230000008569 process Effects 0.000 claims abstract description 101
- LGYIQPOLYWEIQP-UHFFFAOYSA-N 5-methylnon-1-ene Chemical compound CCCCC(C)CCC=C LGYIQPOLYWEIQP-UHFFFAOYSA-N 0.000 claims abstract description 61
- NLQJOZYIKJQMSO-UHFFFAOYSA-N 4-ethenyloctane Chemical compound CCCCC(C=C)CCC NLQJOZYIKJQMSO-UHFFFAOYSA-N 0.000 claims abstract description 49
- PNMREIZXHOBCMA-UHFFFAOYSA-N 4-ethyloct-1-ene Chemical compound CCCCC(CC)CC=C PNMREIZXHOBCMA-UHFFFAOYSA-N 0.000 claims abstract description 49
- SEFXBCYTMUNYFC-UHFFFAOYSA-N 5-methylidenenonane Chemical compound CCCCC(=C)CCCC SEFXBCYTMUNYFC-UHFFFAOYSA-N 0.000 claims abstract description 49
- -1 C12 monoolefins Chemical class 0.000 claims description 400
- 239000003054 catalyst Substances 0.000 claims description 249
- 238000006243 chemical reaction Methods 0.000 claims description 210
- 150000001875 compounds Chemical class 0.000 claims description 201
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 190
- 239000005977 Ethylene Substances 0.000 claims description 190
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims description 165
- 229910052804 chromium Inorganic materials 0.000 claims description 165
- 239000011651 chromium Substances 0.000 claims description 165
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims description 155
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 142
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 124
- 125000002015 acyclic group Chemical group 0.000 claims description 92
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 90
- 239000003446 ligand Substances 0.000 claims description 73
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 59
- 125000004122 cyclic group Chemical group 0.000 claims description 54
- 239000002904 solvent Substances 0.000 claims description 49
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 40
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 40
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 39
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 claims description 38
- 239000003085 diluting agent Substances 0.000 claims description 38
- 239000003795 chemical substances by application Substances 0.000 claims description 37
- 150000004820 halides Chemical class 0.000 claims description 36
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 33
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 claims description 32
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 32
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 30
- 229930195733 hydrocarbon Natural products 0.000 claims description 29
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims description 28
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 claims description 26
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims description 25
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 claims description 24
- QNVRIHYSUZMSGM-UHFFFAOYSA-N hexan-2-ol Chemical compound CCCCC(C)O QNVRIHYSUZMSGM-UHFFFAOYSA-N 0.000 claims description 24
- ZOCHHNOQQHDWHG-UHFFFAOYSA-N hexan-3-ol Chemical compound CCCC(O)CC ZOCHHNOQQHDWHG-UHFFFAOYSA-N 0.000 claims description 24
- 150000002430 hydrocarbons Chemical class 0.000 claims description 24
- WOFPPJOZXUTRAU-UHFFFAOYSA-N 2-Ethyl-1-hexanol Natural products CCCCC(O)CCC WOFPPJOZXUTRAU-UHFFFAOYSA-N 0.000 claims description 22
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 claims description 21
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 claims description 20
- CETWDUZRCINIHU-UHFFFAOYSA-N 2-heptanol Chemical compound CCCCCC(C)O CETWDUZRCINIHU-UHFFFAOYSA-N 0.000 claims description 20
- YVBCULSIZWMTFY-UHFFFAOYSA-N 4-Heptanol Natural products CCCC(O)CCC YVBCULSIZWMTFY-UHFFFAOYSA-N 0.000 claims description 20
- RZKSECIXORKHQS-UHFFFAOYSA-N Heptan-3-ol Chemical compound CCCCC(O)CC RZKSECIXORKHQS-UHFFFAOYSA-N 0.000 claims description 20
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 claims description 20
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims description 18
- 238000007599 discharging Methods 0.000 claims description 16
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 claims description 16
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 15
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 claims description 13
- 229940069096 dodecene Drugs 0.000 claims description 13
- 239000008096 xylene Substances 0.000 claims description 13
- QNVRIHYSUZMSGM-LURJTMIESA-N 2-Hexanol Natural products CCCC[C@H](C)O QNVRIHYSUZMSGM-LURJTMIESA-N 0.000 claims description 12
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 claims description 12
- QQZOPKMRPOGIEB-UHFFFAOYSA-N n-butyl methyl ketone Natural products CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 claims description 12
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 11
- QGVFLDUEHSIZIG-UHFFFAOYSA-N 2-methylheptan-3-ol Chemical compound CCCCC(O)C(C)C QGVFLDUEHSIZIG-UHFFFAOYSA-N 0.000 claims description 10
- NMRPBPVERJPACX-QMMMGPOBSA-N 3-Octanol Natural products CCCCC[C@@H](O)CC NMRPBPVERJPACX-QMMMGPOBSA-N 0.000 claims description 10
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims description 10
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
- SOVOPSCRHKEUNJ-VQHVLOKHSA-N (e)-dec-4-ene Chemical compound CCCCC\C=C\CCC SOVOPSCRHKEUNJ-VQHVLOKHSA-N 0.000 claims description 9
- UURSXESKOOOTOV-UHFFFAOYSA-N dec-5-ene Chemical compound CCCCC=CCCCC UURSXESKOOOTOV-UHFFFAOYSA-N 0.000 claims description 9
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims description 9
- 239000005968 1-Decanol Substances 0.000 claims description 8
- ACUZDYFTRHEKOS-SNVBAGLBSA-N 2-Decanol Natural products CCCCCCCC[C@@H](C)O ACUZDYFTRHEKOS-SNVBAGLBSA-N 0.000 claims description 8
- DTDMYWXTWWFLGJ-JTQLQIEISA-N 4-Decanol Natural products CCCCCC[C@@H](O)CCC DTDMYWXTWWFLGJ-JTQLQIEISA-N 0.000 claims description 8
- ACUZDYFTRHEKOS-UHFFFAOYSA-N decan-2-ol Chemical compound CCCCCCCCC(C)O ACUZDYFTRHEKOS-UHFFFAOYSA-N 0.000 claims description 8
- ICEQLCZWZXUUIJ-UHFFFAOYSA-N decan-3-ol Chemical compound CCCCCCCC(O)CC ICEQLCZWZXUUIJ-UHFFFAOYSA-N 0.000 claims description 8
- DTDMYWXTWWFLGJ-UHFFFAOYSA-N decan-4-ol Chemical compound CCCCCCC(O)CCC DTDMYWXTWWFLGJ-UHFFFAOYSA-N 0.000 claims description 8
- SZMNDOUFZGODBR-UHFFFAOYSA-N decan-5-ol Chemical compound CCCCCC(O)CCCC SZMNDOUFZGODBR-UHFFFAOYSA-N 0.000 claims description 8
- LTHQZRHTXDZWGX-UHFFFAOYSA-N 2-ethyldecan-1-ol Chemical compound CCCCCCCCC(CC)CO LTHQZRHTXDZWGX-UHFFFAOYSA-N 0.000 claims description 7
- ISTVDWLOTXIVAP-UHFFFAOYSA-N 7-methyldecan-2-ol Chemical compound CCCC(C)CCCCC(C)O ISTVDWLOTXIVAP-UHFFFAOYSA-N 0.000 claims description 7
- YUWFEBAXEOLKSG-UHFFFAOYSA-N hexamethylbenzene Chemical compound CC1=C(C)C(C)=C(C)C(C)=C1C YUWFEBAXEOLKSG-UHFFFAOYSA-N 0.000 claims description 6
- 239000000047 product Substances 0.000 description 172
- 238000005829 trimerization reaction Methods 0.000 description 167
- 125000001190 organyl group Chemical group 0.000 description 100
- 125000000524 functional group Chemical group 0.000 description 83
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 69
- 125000001183 hydrocarbyl group Chemical group 0.000 description 68
- DNSUTFANOVPMHS-UHFFFAOYSA-N [Cr].[PH2](=O)N=C(N)N Chemical compound [Cr].[PH2](=O)N=C(N)N DNSUTFANOVPMHS-UHFFFAOYSA-N 0.000 description 65
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 61
- OGHNLHBJKILTCF-UHFFFAOYSA-N NC(N)=N[PH2]=O Chemical group NC(N)=N[PH2]=O OGHNLHBJKILTCF-UHFFFAOYSA-N 0.000 description 54
- 239000001257 hydrogen Substances 0.000 description 53
- 229910052739 hydrogen Inorganic materials 0.000 description 53
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 50
- 125000001424 substituent group Chemical group 0.000 description 47
- 125000000217 alkyl group Chemical group 0.000 description 39
- XCNKRVSJEUZLFH-UHFFFAOYSA-N [PH2](=O)N=CN.[Cr] Chemical compound [PH2](=O)N=CN.[Cr] XCNKRVSJEUZLFH-UHFFFAOYSA-N 0.000 description 37
- 229910052799 carbon Inorganic materials 0.000 description 37
- 229910052757 nitrogen Inorganic materials 0.000 description 36
- 125000004433 nitrogen atom Chemical group N* 0.000 description 36
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 35
- 229910052751 metal Inorganic materials 0.000 description 33
- 239000002184 metal Substances 0.000 description 33
- MVQPZQCAIOBANX-UHFFFAOYSA-N [PH2](=O)N=CN Chemical group [PH2](=O)N=CN MVQPZQCAIOBANX-UHFFFAOYSA-N 0.000 description 29
- 125000003118 aryl group Chemical group 0.000 description 29
- 125000005568 organylene group Chemical group 0.000 description 27
- 150000001721 carbon Chemical group 0.000 description 25
- 125000004432 carbon atom Chemical group C* 0.000 description 21
- 230000007935 neutral effect Effects 0.000 description 21
- 239000013638 trimer Substances 0.000 description 21
- 125000005647 linker group Chemical group 0.000 description 20
- 229910052736 halogen Inorganic materials 0.000 description 19
- 238000010791 quenching Methods 0.000 description 19
- 150000002367 halogens Chemical class 0.000 description 18
- 150000001335 aliphatic alkanes Chemical class 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 15
- 125000000743 hydrocarbylene group Chemical group 0.000 description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 13
- 239000004215 Carbon black (E152) Substances 0.000 description 13
- 125000001931 aliphatic group Chemical group 0.000 description 13
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 13
- ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine group Chemical group NC(=N)N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 13
- 238000006384 oligomerization reaction Methods 0.000 description 13
- 125000000962 organic group Chemical group 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 125000005234 alkyl aluminium group Chemical group 0.000 description 12
- 150000007942 carboxylates Chemical group 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 229910001507 metal halide Inorganic materials 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- 125000000320 amidine group Chemical group 0.000 description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 11
- 150000002825 nitriles Chemical class 0.000 description 11
- PAPNRQCYSFBWDI-UHFFFAOYSA-N 2,5-Dimethyl-1H-pyrrole Chemical compound CC1=CC=C(C)N1 PAPNRQCYSFBWDI-UHFFFAOYSA-N 0.000 description 10
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical group [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 10
- 239000004711 α-olefin Substances 0.000 description 10
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 8
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 8
- 125000004836 hexamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 8
- 150000002736 metal compounds Chemical class 0.000 description 8
- 150000005309 metal halides Chemical class 0.000 description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 8
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 7
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
- 150000007824 aliphatic compounds Chemical class 0.000 description 7
- 150000001409 amidines Chemical class 0.000 description 7
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- IGJQUJNPMOYEJY-UHFFFAOYSA-N 2-acetylpyrrole Chemical compound CC(=O)C1=CC=CN1 IGJQUJNPMOYEJY-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 6
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
- QPDLRYXFENXPPC-UHFFFAOYSA-N chromium;1h-pyrrole Chemical compound [Cr].C=1C=CNC=1 QPDLRYXFENXPPC-UHFFFAOYSA-N 0.000 description 6
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 6
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 6
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 6
- CMAOLVNGLTWICC-UHFFFAOYSA-N 2-fluoro-5-methylbenzonitrile Chemical compound CC1=CC=C(F)C(C#N)=C1 CMAOLVNGLTWICC-UHFFFAOYSA-N 0.000 description 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 150000002009 diols Chemical class 0.000 description 5
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 229920005862 polyol Polymers 0.000 description 5
- 150000003077 polyols Chemical class 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 5
- ORYGRKHDLWYTKX-UHFFFAOYSA-N trihexylalumane Chemical compound CCCCCC[Al](CCCCCC)CCCCCC ORYGRKHDLWYTKX-UHFFFAOYSA-N 0.000 description 5
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 229910002651 NO3 Inorganic materials 0.000 description 4
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 125000004104 aryloxy group Chemical group 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 150000004696 coordination complex Chemical class 0.000 description 4
- 230000009849 deactivation Effects 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 4
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 4
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 4
- 125000006606 n-butoxy group Chemical group 0.000 description 4
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 4
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- ZSKGQVFRTSEPJT-UHFFFAOYSA-N pyrrole-2-carboxaldehyde Chemical compound O=CC1=CC=CN1 ZSKGQVFRTSEPJT-UHFFFAOYSA-N 0.000 description 4
- WRHZVMBBRYBTKZ-UHFFFAOYSA-N pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC=CN1 WRHZVMBBRYBTKZ-UHFFFAOYSA-N 0.000 description 4
- 150000003233 pyrroles Chemical class 0.000 description 4
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- 239000001301 oxygen Substances 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-M pentadecanoate Chemical compound CCCCCCCCCCCCCCC([O-])=O WQEPLUUGTLDZJY-UHFFFAOYSA-M 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- DVMZCYSFPFUKKE-UHFFFAOYSA-K scandium chloride Chemical compound Cl[Sc](Cl)Cl DVMZCYSFPFUKKE-UHFFFAOYSA-K 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- AIFMYMZGQVTROK-UHFFFAOYSA-N silicon tetrabromide Chemical compound Br[Si](Br)(Br)Br AIFMYMZGQVTROK-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000005922 tert-pentoxy group Chemical group 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IEXRMSFAVATTJX-UHFFFAOYSA-N tetrachlorogermane Chemical compound Cl[Ge](Cl)(Cl)Cl IEXRMSFAVATTJX-UHFFFAOYSA-N 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- SZHOJFHSIKHZHA-UHFFFAOYSA-M tridecanoate Chemical compound CCCCCCCCCCCCC([O-])=O SZHOJFHSIKHZHA-UHFFFAOYSA-M 0.000 description 1
- 150000005671 trienes Chemical class 0.000 description 1
- FTBATIJJKIIOTP-UHFFFAOYSA-K trifluorochromium Chemical compound F[Cr](F)F FTBATIJJKIIOTP-UHFFFAOYSA-K 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
- KPGXUAIFQMJJFB-UHFFFAOYSA-H tungsten hexachloride Chemical compound Cl[W](Cl)(Cl)(Cl)(Cl)Cl KPGXUAIFQMJJFB-UHFFFAOYSA-H 0.000 description 1
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
- C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
- C07C2/08—Catalytic processes
- C07C2/26—Catalytic processes with hydrides or organic compounds
- C07C2/32—Catalytic processes with hydrides or organic compounds as complexes, e.g. acetyl-acetonates
- C07C2/34—Metal-hydrocarbon complexes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
- C07C2/88—Growth and elimination reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/02—Alkenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- C07C2531/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- C07C2531/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- C07C2531/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- C07C2531/22—Organic complexes
Definitions
- the present disclosure relates to compositions containing decene isomers and methods of making same. More specifically, the present disclosure relates to compositions containing decene isomers produced in an ethylene oligomerization process.
- Olefins such as decenes
- Commercial 1-decene has many potential uses and 1-decene demand can often out-pace 1-decene supply.
- many applications may not require a feedstock having a high 1-decene content and compositions containing a mixture of decene isomers can be utilized in particular applications depending upon the quantity and identity of the components found in the compositions containing the decene isomers.
- Embodiments disclosed and described herein are directed to a composition
- a composition comprising a) at least 76 mol% C 10 monoolefins, the C 10 monoolefins comprising i) at least 3 mol% 2-butyl-1-hexene, ii) at least 8 mol% 3-propyl-1-heptene, iii) at least 6 mol% 4-ethyl-1-octene, and iv) at least 20 mol% 5-methyl-1-nonene; and b) at least 1 mol% C 14 monoolefins.
- compositions comprising at least 95 mol% C 10 monoolefins, the C 10 monoolefins comprising i) at least 3 mol% 2-butyl-1-hexene, ii) at least 10 mol% 3-propyl-1-heptene, iii) at least 7 mol% 4-ethyl-1-octene, and iv) at least 24 mol% 5-methyl-1-nonene.
- compositions comprising at least 76 mol% C 10 monoolefins. Also disclosed herein are compositions comprising at least 95 mol% C 10 monoolefins.
- a process for producing a C 10 monoolefins composition can comprise (a) contacting 1) ethylene, 2) a catalyst system comprising i) a chromium containing compound, ii) a heteroatomic ligand, and iii) a metal alkyl compound, and 3) optionally a reaction system diluent; (b) forming an oligomer product comprising 1-hexene and/or 1-octene in a reaction system; (c) discharging a reaction system effluent from the reaction system; (d) contacting the reaction system effluent with a catalyst system deactivating agent; and (e) isolating a first composition comprising at least 76 mol% C 10 monoolefins.
- the process can comprise isolating a second composition comprising at least 95 mol% C 10 monoolefins. In other embodiments, the process can comprise recovering a second composition comprising at least 95 mol% C 10 monoolefins from the first composition comprising at least 76 mol% C 10 monoolefins.
- Groups of elements of the Periodic Table are indicated using the numbering scheme indicated in the version of the Periodic Table of elements published in Chemical and Engineering News, 63(5), 27, 1985 .
- a group of elements can be indicated using a common name assigned to the group; for example, alkali metals for Group 1 elements, alkaline earth metals (or alkaline metals) for Group 2 elements, transition metals for Groups 3-12 elements, and halogens for Group 17 elements.
- transitional term “comprising”, which is synonymous with “including,” “containing,” “having,” or “characterized by,” is inclusive or openended and does not exclude additional, unrecited elements or method steps.
- a feedstock consisting essentially of a material A can include impurities typically present in a commercially produced or commercially available sample of the recited compound or composition.
- a claim includes different features and/or feature classes (for example, a method step, feedstock features, and/or product features, among other possibilities), the transitional terms comprising, consisting essentially of, and consisting of apply only to the feature class to which is utilized and it is possible to have different transitional terms or phrases utilized with different features within a claim.
- a method can comprise several recited steps (and other non-recited steps), but utilize a catalyst system preparation consisting of specific steps, or alternatively, consisting essentially of specific steps, but utilize a catalyst system comprising recited components and other non-recited components.
- compositions and methods are described in terms of “comprising” (or other broad term) various components and/or steps, the compositions and methods can also be described using narrower terms, such as “consist essentially of' or “consist of' the various components and/or steps.
- a trialkylaluminum compound is meant to encompass one trialkylaluminum compound, or mixtures or combinations of more than one trialkylaluminum compound, unless otherwise specified.
- a general reference to a compound includes all structural isomers, unless explicitly indicated otherwise; e.g., a general reference to pentane includes n-pentane, 2-methyl-butane, and 2,2-dimethylpropane, while a general reference to a butyl group includes an n-butyl group, a sec-butyl group, an iso-butyl group, and a tert-butyl group.
- any general formula or name presented also encompasses all conformational isomers, regioisomers, and stereoisomers that can arise from a particular set of substituents.
- a chemical "group” is described according to how that group is formally derived from a reference or "parent" compound, for example, by the number of hydrogen atoms formally removed from the parent compound to generate the group, even if that group is not literally synthesized in this manner.
- an "alkyl group” can formally be derived by removing one hydrogen atom from an alkane
- an “alkylene group” can formally be derived by removing two hydrogen atoms from an alkane.
- a more general term can be used to encompass a variety of groups that formally are derived by removing any number ("one or more") of hydrogen atoms from a parent compound, which in this example can be described as an "alkane group,” and which encompasses an "alkyl group,” an “alkylene group,” and materials having three or more hydrogens atoms, as necessary for the situation, removed from the alkane.
- alkane group an "alkane group”
- alkyl group an "alkylene group”
- materials having three or more hydrogens atoms, as necessary for the situation, removed from the alkane removed from the alkane.
- substituent, ligand, or other chemical moiety that can constitute a particular "group” implies that the well-known rules of chemical structure and bonding are followed when that group is employed as described.
- organic group is used herein in accordance with the definition specified by IUPAC: an organic substituent group, regardless of functional type, having one free valence at a carbon atom.
- an "organylene group” refers to an organic group, regardless of functional type, derived by removing two hydrogen atoms from one or two carbon atoms of an organic compound, either two hydrogen atoms from one carbon atom or one hydrogen atom from each of two different carbon atoms.
- An “organic group” refers to a generalized group formed by removing one or more hydrogen atoms from carbon atoms of an organic compound.
- an "organyl group,” an “organylene group,” and an “organic group” can contain organic functional group(s) and/or atom(s) other than carbon and hydrogen, that is, an organic group can comprise functional groups and/or atoms in addition to carbon and hydrogen.
- organic functional group(s) and/or atom(s) other than carbon and hydrogen include halogens, oxygen, nitrogen, phosphorus, and the like.
- functional groups include ethers, aldehydes, ketones, esters, sulfides, amines, phosphines, and so forth.
- a functional group for example, an acyl group (-C(O)R), a formyl group (-C(O)H), a carboxy group (-C(O)OH), a hydrocarboxycarbon
- the hydrogen atom(s) removed to form the "organyl group,” “organylene group,” or “organic group” can be attached to a carbon atom not belonging to, and remote from, a functional group, for example, -CH 2 C(O)CH 3 , -CH 2 NR 2 , and the like.
- An "organyl group,” “organylene group,” or “organic group” can be aliphatic, inclusive of being cyclic or acyclic, or can be aromatic.
- Organicyl groups,” “organylene groups,” and “organic groups” also encompass heteroatom-containing rings, heteroatom-containing ring systems, heteroaromatic rings, and heteroaromatic ring systems.
- Organic groups can be linear or branched unless otherwise specified.
- organyl group “organylene group,” or “organic group” definitions include “hydrocarbyl group,” “hydrocarbylene group,” “hydrocarbon group,” respectively, and “alkyl group,” “alkylene group,” and “alkane group,” respectively, as members.
- organyl group consisting of inert functional groups refers to an organyl group wherein the organic functional group(s) and/or atom(s) other than carbon and hydrogen present in the functional group are restricted to those functional group(s) and/or atom(s) other than carbon and hydrogen which do not complex with a metal compound and/or are inert under the process conditions defined herein.
- organyl group consisting of inert functional groups further defines the particular organyl groups that can be present within the organyl group consisting of inert functional groups.
- organyl group consisting of inert functional groups can refer to the presence of one or more inert functional groups within the organyl group.
- organyl group consisting of inert functional groups definition includes the hydrocarbyl group as a member (among other groups).
- an "organylene group consisting of inert functional groups” refers to an organic group formed by removing two hydrogen atoms from one or two carbon atoms of an organic compound consisting of inert functional groups and an "organic group consisting of inert functional groups” refers to a generalized organic group consisting of inert functional groups formed by removing one or more hydrogen atoms from one or more carbon atoms of an organic compound consisting of inert functional groups.
- an "inert functional group” is a group which does not substantially interfere with the process described herein in which the material having an inert functional group takes part and/or does not complex with a metal compound of a metal complex.
- the term “does not complex with the metal compound” can include groups that could complex with a metal compound but in particular molecules described herein may not complex with a metal compound due to its positional relationship within a ligand.
- an ether group located at a para position of a substituted phenyl phosphinyl group may be an inert functional group because a single metal compound cannot complex with both the para ether group and the N 2 -phosphinyl formamidine group of the same metal complex molecule.
- the inertness of a particular functional group is not only related to the functional group's inherent inability to complex the metal compound, but can also be related to the functional group's position within the metal complex.
- Non-limiting examples of inert functional groups which do not substantially interfere with processes described herein can include halo (fluoro, chloro, bromo, and iodo), nitro, hydrocarboxy groups (e.g., alkoxy, and/or aroxy, among others), sulfidyl groups, and/or hydrocarbyl groups, among others.
- hydrocarbon whenever used in this specification and claims refers to a compound containing only carbon and hydrogen. Other identifiers can be utilized to indicate the presence of particular groups in the hydrocarbon (e.g., halogenated hydrocarbon indicates the presence of one or more halogen atoms replacing an equivalent number of hydrogen atoms in the hydrocarbon).
- hydrocarbyl group is used herein in accordance with the definition specified by IUPAC: a univalent group formed by removing a hydrogen atom from a hydrocarbon.
- Non-limiting examples of hydrocarbyl groups include ethyl, phenyl, tolyl, propenyl, and the like.
- a “hydrocarbylene group” refers to a group formed by removing two hydrogen atoms from a hydrocarbon, either two hydrogen atoms from one carbon atom or one hydrogen atom from each of two different carbon atoms. Therefore, in accordance with the terminology used herein, a “hydrocarbon group” refers to a generalized group formed by removing one or more hydrogen atoms (as necessary for the particular group) from a hydrocarbon.
- a “hydrocarbyl group,” “hydrocarbylene group,” and “hydrocarbon group” can be acyclic or cyclic groups, and/or can be linear or branched.
- hydrocarbyl group can include rings, ring systems, aromatic rings, and aromatic ring systems, which contain only carbon and hydrogen.
- Hydrocarbyl groups include, by way of example, aryl, arylene, arene, alkyl, alkylene, alkane, cycloalkyl, cycloalkylene, cycloalkane, aralkyl, aralkylene, and aralkane groups, among other groups, as members.
- alkane whenever used in this specification and claims refers to a saturated hydrocarbon compound. Other identifiers can be utilized to indicate the presence of particular groups in the alkane (e.g., halogenated alkane indicates the presence of one or more halogen atoms replacing an equivalent number of hydrogen atoms in the alkane).
- alkyl group is used herein in accordance with the definition specified by IUPAC: a univalent group formed by removing a hydrogen atom from an alkane.
- an “alkylene group” refers to a group formed by removing two hydrogen atoms from an alkane (either two hydrogen atoms from one carbon atom or one hydrogen atom from two different carbon atoms).
- alkane group is a general term that refers to a group formed by removing one or more hydrogen atoms (as necessary for the particular group) from an alkane.
- An “alkyl group,” “alkylene group,” and “alkane group” can be acyclic or cyclic groups, and/or can be linear or branched unless otherwise specified.
- Primary, secondary, and tertiary alkyl group are derived by removal of a hydrogen atom from a primary, secondary, and tertiary carbon atom, respectively, of an alkane.
- the n-alkyl group can be derived by removal of a hydrogen atom from a terminal carbon atom of a linear alkane.
- An aliphatic compound is an acyclic or cyclic, saturated or unsaturated carbon compound, excluding aromatic compounds.
- an aliphatic compound is an acyclic or cyclic, saturated or unsaturated carbon compound, excluding aromatic compounds; that is, an aliphatic compound is a non-aromatic organic compound.
- An "aliphatic group” is a generalized group formed by removing one or more hydrogen atoms (as necessary for the particular group) from a carbon atom of an aliphatic compound.
- an aliphatic compound is an acyclic or cyclic, saturated or unsaturated carbon compound, excluding aromatic compounds. That is, an aliphatic compound is a non-aromatic organic compound.
- Aliphatic compounds and therefore aliphatic groups can contain organic functional group(s) and/or atom(s) other than carbon and hydrogen.
- substituted when used to describe a compound or group, for example, when referring to a substituted analog of a particular compound or group, is intended to describe any non-hydrogen moiety that formally replaces a hydrogen in that group, and is intended to be non-limiting.
- a group or groups can also be referred to herein as “unsubstituted” or by equivalent terms, such as “non-substituted,” which refers to the original group in which a non-hydrogen moiety does not replace a hydrogen within that group.
- “Substituted” is intended to be non-limiting and include inorganic substituents or organic substituents.
- olefin whenever used in this specification and claims refers to hydrocarbons that have at least one carbon-carbon double bond that is not part of an aromatic ring or an aromatic ring system.
- olefin includes aliphatic and aromatic, cyclic and acyclic, and/or linear and branched hydrocarbons having at least one carbon-carbon double bond that is not part of an aromatic ring or ring system unless specifically stated otherwise. Olefins having only one, only two, only three, etc., carbon-carbon double bonds can be identified by use of the term “mono,” "di,” “tri,” etc., within the name of the olefin. The olefins can be further identified by the position of the carbon-carbon double bond(s).
- alkene whenever used in this specification and claims refers to a linear or branched aliphatic hydrocarbon olefin that has one or more carbon-carbon double bonds. Alkenes having only one, only two, only three, etc., such multiple bonds can be identified by use of the term “mono,” “di,” “tri,” etc., within the name.
- alkamonoenes, alkadienes, and alkatrienes refer to linear or branched acyclic hydrocarbon olefins having only one carbon-carbon double bond (acyclic having a general formula of C n H 2n ), only two carbon-carbon double bonds (acyclic having a general formula of C n H 2n-2 ), and only three carbon-carbon double bonds (acyclic having a general formula of C n H 2n-4 ), respectively.
- Alkenes can be further identified by the position of the carbon-carbon double bond(s). Other identifiers can be utilized to indicate the presence or absence of particular groups within an alkene.
- a haloalkene refers to an alkene having one or more hydrogen atoms replaced with a halogen atom.
- alpha olefin refers to an olefin that has a carbon-carbon double bond between the first and second carbon atoms of the longest contiguous chain of carbon atoms.
- alpha olefin includes linear and branched alpha olefins unless expressly stated otherwise. In the case of branched alpha olefins, a branch can be at the 2 position (a vinylidene) and/or the 3 position or higher with respect to the olefin double bond.
- vinylidene a branch can be at the 2 position (a vinylidene) and/or the 3 position or higher with respect to the olefin double bond.
- vinylidene a branch at the 2 position with respect to the olefin double bond.
- vinylene whenever used in this specification and claims refers to an alpha olefin having a branch at the 2 position with respect to the olefin double bond.
- alpha olefin does not indicate the presence or
- normal alpha olefin whenever used in this specification and claims refers to a linear aliphatic mono-olefin having a carbon-carbon double bond between the first and second carbon atoms. It is noted that "normal alpha olefin” is not synonymous with “linear alpha olefin” as the term “linear alpha olefin” can include linear olefinic compounds having a double bond between the first and second carbon atoms.
- room temperature or “ambient temperature” are used herein to describe any temperature from 15 °C to 35 °C wherein no external heat or cooling source is directly applied to the reaction vessel. Accordingly, the terms “room temperature” and “ambient temperature” encompass the individual temperatures and any and all ranges, subranges, and combinations of subranges of temperatures from 15 °C to 35 °C wherein no external heating or cooling source is directly applied to the reaction vessel.
- atmospheric pressure is used herein to describe an earth air pressure wherein no external pressure modifying means is utilized. Generally, unless practiced at extreme earth altitudes, “atmospheric pressure” is about 1 atmosphere (alternatively, about 14.7 psi or about 101 kPa).
- references to substitution patterns are taken to indicate that the indicated group(s) is (are) located at the indicated position and that all other non-indicated positions are hydrogen.
- reference to a 4-substituted phenyl group indicates that there is a non-hydrogen substituent located at the 4 position and hydrogens located at the 2, 3, 5, and 6 positions.
- reference to a 3-substituted naphth-2-yl indicates that there is a non-hydrogen substituent located at the 3 position and hydrogens located at the 1, 4, 5, 6, 7, and 8 positions.
- references to compounds or groups having substitutions at positions in addition to the indicated position will be referenced using comprising or some other alternative language.
- a reference to a phenyl group comprising a substituent at the 4 position refers to a phenyl group having a non-hydrogen substituent group at the 4 position and hydrogen or any non-hydrogen group at the 2, 3, 5, and 6 positions.
- any carbon-containing group for which the number of carbon atoms is not specified can have, according to proper chemical practice, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30 carbon atoms, or any range or combination of ranges between these values.
- any carbon-containing group can have from 1 to 30 carbon atoms, from 1 to 25 carbon atoms, from 1 to 20 carbon atoms, from 1 to 15 carbon atoms, from 1 to 10 carbon atoms, or from 1 to 5 carbon atoms.
- other identifiers or qualifying terms can be utilized to indicate the presence or absence of a particular substituent, a particular regiochemistry and/or stereochemistry, or the presence or absence of a branched underlying structure or backbone.
- Processes and/or methods described herein utilize steps, features, and compounds which are independently described herein.
- the process and methods described herein may or may not utilize step identifiers (e.g., 1), 2), etc., a), b), etc., or i), ii), etc.), features (e.g., 1), 2), etc., a), b), etc., or i), ii), etc.), and/or compound identifiers (e.g., first, second, etc.).
- step identifiers e.g., 1), 2), etc., a), b), etc., or i), ii), etc.
- features e.g., 1), 2), etc., a), b), etc., or i), ii), etc.
- compound identifiers e.g., first, second, etc.
- processes and/or methods described herein can have multiple steps, features (e.g., reagent ratios, formation conditions
- step or feature identifier e.g., 1), 2), etc., a), b), etc., or i), ii), etc.
- compound identifier e.g., first, second, etc.
- step or feature identifiers can be added and/or modified to indicate individual different steps/features/compounds utilized within the process and/or methods without detracting from the general disclosure.
- Embodiments disclosed herein can provide the materials listed as suitable for satisfying a particular feature of the embodiment delimited by the term "or.”
- a particular feature of the disclosed subject matter can be disclosed as follows: Feature X can be A, B, or C. It is also contemplated that for each feature the statement can also be phrased as a listing of alternatives such that the statement "Feature X is A, alternatively B, or alternatively C" is also an embodiment of the present disclosure whether or not the statement is explicitly recited.
- compositions described herein can comprise C 10 monoolefins.
- a monoolefin is a linear or branched aliphatic hydrocarbon olefin that has one and only one carbon-carbon double bond.
- a C n monoolefin is a linear or branched aliphatic hydrocarbon olefin that has n and only n carbon atoms, and one and only one carbon-carbon double bond.
- a C 10 monoolefin is a linear or branched aliphatic hydrocarbon olefin that has ten and only ten carbon atoms, and one and only one carbon-carbon double bond.
- the composition disclosed herein can comprise (a) at least 76 mol%, at least 78 mol%, at least 80 mol%, or at least 82 mol% C 10 monoolefins, and (b) at least 1 mol%, at least 2 mol%, at least 3 mol%, or at least 4 mol% C 14 monoolefins.
- compositions disclosed herein can comprise (a) from 76 mol% to 92 mol%, from 78 mol% to 90 mol%, from 80 mol% to 88 mol%, or from 82 mol% to 86 mol% C 10 monoolefins; and (b) from 1 mol% to 12 mol%, from 2 mol% to 10 mol%, from 3 mol% to 8 mol%, or from 4 mol% to 7 mol% C 14 monoolefins.
- a composition comprising (a) at least 76 mol% C 10 monoolefins, and (b) at least 1 mol% C 14 monoolefins can also be referred to as a "first composition” or "first compositions.”
- composition(s) disclosed herein can comprise at least 95 mol%, at least 96 mol%, at least 97 mol%, at least 98 mol%, or at least 99 mol% C 10 monoolefins.
- a composition comprising at least 95 mol% C 10 monoolefins can also be referred to as a "second composition” or "second compositions.”
- C 10 monoolefins are described herein (e.g., identity and molar amounts of specific C 10 monoolefins and molar ratios of specific C 10 monoolefins, among other C 10 monoolefins features). These C 10 monoolefin embodiments can be used without limitation to further describe any composition disclosed herein comprising C 10 monoolefins disclosed herein (e.g., the "first composition” or the "second composition”).
- the C 10 monoolefins of any composition comprising C 10 monoolefins described herein can comprise, can consist essentially of, or can be, 2-butyl-1-hexene, 3-propyl-1-heptene, 4-ethyl-1-octene, and 5-methyl-1-nonene.
- the C 10 monoolefins of any composition comprising C 10 monoolefins described herein can comprise i) at least 3 mol%, at least 4 mol%, at least 5 mol%, at least 6 mol%, at least 7 mol%, or at least 8 mol% 2-butyl-1-hexene; ii) at least 8 mol%, at least 9 mol%, at least 10 mol%, at least 11 mol%, at least 12 mol%, or at least 13 mol% 3-propyl-1-heptene; iii) at least 6 mol%, at least 7 mol%, at least 8 mol%, at least 9 mol%, at least 10 mol%, or at least 11 mol% 4-ethyl-1-octene; and iv) at least 20 mol%, at least 22 mol%, at least 24 mol%, at least 26 mol%, at least 28 mol%, or at least 30 mol% 5-methyl-1-n
- the C 10 monoolefins of any composition comprising C 10 monoolefins described herein can comprise from 3 mol% to 20 mol%, from 4 mol% to 18 mol%, from 5 mol% to 17 mol%, from 6 mol% to 16 mol%, or from 7 mol% to 15 mol% 2-butyl-1-hexene.
- the C 10 monoolefins of any composition comprising C 10 monoolefins described herein can comprise from 10 mol% to 32 mol%, from 11 mol% to 30 mol%, from 12 mol% to 28 mol%, from 13 mol% to 26 mol%, or from 14 mol% to 24 mol% 3-propyl-1-heptene.
- the C 10 monoolefins of any composition comprising C 10 monoolefins described herein can comprise from 7 mol% to 25 mol%, from 8 mol% to 24 mol%, from 9 mol% to 23 mol%, from 10 mol% to 22 mol%, or from 11 mol% to 21 mol% 4-ethyl-1-octene.
- the C 10 monoolefins of any composition comprising C 10 monoolefins described herein can comprise from 24 mol% to 52 mol%, from 26 mol% to 50 mol%, from 28 mol% to 48 mol%, from 30 mol% to 46 mol%, or from 32 mol% to 44 mol% 5-methyl-1-nonene.
- the C 10 monoolefins of any composition comprising C 10 monoolefins described herein can comprise i) from 3 mol% to 20 mol%, from 4 mol% to 18 mol%, from 5 mol% to 17 mol%, from 6 mol% to 16 mol%, or from 7 mol% to 15 mol% 2-butyl-1-hexene; ii) from 10 mol% to 32 mol%, from 11 mol% to 30 mol%, from 12 mol% to 28 mol%, from 13 mol% to 26 mol%, or from 14 mol% to 24 mol% 3-propyl-1-heptene; iii) from 7 mol% to 25 mol%, from 8 mol% to 24 mol%, from 9 mol% to 23 mol%, from 10 mol% to 22 mol%, or from 11 mol% to 21 mol% 4-ethyl-1-octene; and iv) from 24 mol% to 52
- the C 10 monoolefins of any composition comprising C 10 monoolefins described herein can have a molar ratio of 5-methyl-1-nonene to 2-butyl-1-hexene of at least 2:1, at least 2.4:1, at least 2.6:1, or at least 2.8:1.
- the C 10 monoolefins of any composition comprising C 10 monoolefins described herein can have a molar ratio of 5-methyl-1-nonene to 3-propyl-1-heptene of at least 1.2:1, at least 1.4:1, at least 1.6:1, or at least 1.8:1.
- the C 10 monoolefins of any composition comprising C 10 monoolefins described herein can have molar ratio of 5-methyl-1-nonene to 4-ethyl-1-octene of at least 1.6:1, at least 1.7:1, at least 1.9:1, or at least 2.1:1.
- the C 10 monoolefins of any composition comprising C 10 monoolefins described herein can have a molar ratio of 5-methyl-1-nonene to 2-butyl-1-hexene of at least 2:1, at least 2.4:1, at least 2.6:1, or at least 2.8:1; a molar ratio of 5-methyl-1-nonene to 3-propyl-1-heptene of at least 1.2:1, at least 1.4:1, at least 1.6:1, or at least 1.8:1; and a molar ratio of 5-methyl-1-nonene to 4-ethyl-1-octene of at least 1.6:1, at least 1.7:1, at least 1.9:1, or at least 2.1:1.
- the C 10 monoolefins of any composition comprising C 10 monoolefins described herein can comprise linear C 10 monoolefins.
- the linear C 10 monoolefins can comprise, can consist essentially of, or can be, 1-decene, 4-decene, 5-decene, or combinations thereof; alternatively, 1-decene; alternatively, 4-decene and/or 5-decene; alternatively, 4-decene; or alternatively, 5-decene.
- the C 10 monoolefins of any composition comprising C 10 monoolefins described herein can comprise less than or equal to 26 mol%, less than or equal to 24 mol%, less than or equal to 22 mol%, less than or equal to 20 mol%, or less than or equal to 18 mol% linear C 10 monoolefins.
- the C 10 monoolefins of any composition comprising C 10 monoolefins described herein can comprise from 1 mol% to 16 mol%, from 2 mol% to 15 mol%, from 3 mol% to 14 mol%, from 4 mol% to 13 mol%, or from 6 mol% to 12 mol% 4-decene and/or 5-decene.
- the C 10 monoolefins of any composition comprising C 10 monoolefins described herein can comprise less than or equal to 10 mol%, less than or equal to 9 mol%, less than or equal to 8 mol%, less than or equal to 7 mol%, or less than or equal to 6 mol% 1-decene. In other embodiments, the C 10 monoolefins of any composition comprising C 10 monoolefins described herein can comprise from 0.5 mol% to 9 mol%, from 1 mol% to 8 mol%, from 1.5 mol% to 7 mol%, or from 2 mol% to 6 mol% 1-decene.
- the first compositions disclosed herein can further comprise C 9- monoolefins, C 11+ monoolefins, or combinations thereof; alternatively, C 9- monoolefins; or alternatively, C 11+ monoolefins.
- the C 9- monoolefins can comprise, can consist essentially of, or can be, a C 7 monoolefin, a C 8 monoolefin, a C 9 monoolefin, or combinations thereof; alternatively, a C 7 monoolefin; alternatively, a C 8 monoolefin; or alternatively, a C 9 monoolefin.
- the C 9- monoolefins can comprise, can consist essentially of, or can be, a C 8 monoolefin.
- the C 11+ monoolefins can comprise, can consist essentially of, or can be, a C 11 monoolefin, a C 12 monoolefin, a C 13 monoolefin, a C 14 monoolefin, a C 15 monoolefin, a C 16 monoolefin, a C 17 monoolefin, a C 18 monoolefin, or combinations thereof; alternatively, a C 11 monoolefin; alternatively, a C 12 monoolefin; alternatively, a C 13 monoolefin; alternatively, a C 14 monoolefin; alternatively, a C 15 monoolefin; alternatively, a C 16 monoolefin; alternatively, a C 17 monoolefin; or alternatively, a C 18 monoolefin.
- the C 11+ monoolefins can comprise, can consist essentially of, or can be, a C 12 monoolefin, a C 16 monoolefin, a C 18 monoolefin, or combinations thereof; alternatively, a C 12 monoolefin; alternatively, a C 16 monoolefin; or alternatively, a C 18 monoolefin.
- the first compositions disclosed herein can further comprise C 8 monoolefins, C 12 monoolefins, C 16 monoolefins, C 18 monoolefins, or combinations thereof; alternatively, C 8 monoolefins; alternatively, C 12 monoolefins; alternatively, C 16 monoolefins and/or C 18 monoolefins; alternatively, C 16 monoolefins; or alternatively, C 18 monoolefins.
- the C 8 monoolefins can comprise 1-octene.
- the C 12 monoolefins can comprise 1-dodecene.
- the first compositions disclosed herein can further comprise from 0.1 mol% to 5 mol%, from 0.25 mol% to 4 mol%, or from 0.5 mol% to 3 mol% C 8 monoolefins.
- the C 8 monoolefins can comprise at least 95 mol%, at least 96 mol%, at least 97 mol%, at least 98 mol%, or at least 99 mol% 1-octene.
- the first compositions disclosed herein can further comprise from 0.1 mol% to 5 mol%, from 0.25 mol% to 4 mol%, or from 0.5 mol% to 3 mol% C 12 monoolefins.
- the C 12 monoolefins can comprise from 54 mol% to 74 mol%, from 56 mol% to 72 mol%, from 58 mol% to 70 mol%, or from 60 mol% to 68 mol% 1-dodecene.
- the first compositions disclosed herein can further comprise from 0.05 mol% to 2 mol%, from 0.04 mol% to 1.5 mol%, from 0.06 mol% to 1.25 mol%, from 0.08 mol% to 1 mol%, or from 0.1 mol% to 0.75 mol% C 16 monoolefins and/or C 18 monoolefins
- the first compositions disclosed herein can further comprise saturated hydrocarbons.
- the saturated hydrocarbons can comprise, can consist essentially of, or can be, acyclic saturated hydrocarbons, cyclic saturated hydrocarbons, or combinations thereof; alternatively, acyclic saturated hydrocarbons; or alternatively, cyclic saturated hydrocarbons.
- the acyclic saturated hydrocarbons can comprise, can consist essentially of, or can be, a C 7 to C 18 acyclic saturated hydrocarbon.
- the C 7 to C 18 acyclic saturated hydrocarbon can comprise, can consist essentially of, or can be, a C 7 acyclic saturated hydrocarbon, a C 8 acyclic saturated hydrocarbon, a C 9 acyclic saturated hydrocarbon, a C 10 acyclic saturated hydrocarbon, a C 11 acyclic saturated hydrocarbon, a C 12 acyclic saturated hydrocarbon, a C 13 acyclic saturated hydrocarbon, a C 14 acyclic saturated hydrocarbon, a C 15 acyclic saturated hydrocarbon, a C 16 acyclic saturated hydrocarbon, a C 17 acyclic saturated hydrocarbon, a C 18 acyclic saturated hydrocarbon, or combinations thereof; alternatively, a C 7 acyclic saturated hydrocarbon; alternatively, a C 8 acyclic saturated hydrocarbon; alternatively, a C
- the C 7 to C 18 acyclic saturated hydrocarbon can comprise, can consist essentially of, or can be, a C 8 acyclic saturated hydrocarbon, a C 10 acyclic saturated hydrocarbon, a C 12 acyclic saturated hydrocarbon, a C 14 acyclic saturated hydrocarbon, a C 16 acyclic saturated hydrocarbon, a C 18 acyclic saturated hydrocarbon, or combinations thereof.
- the C 7 to C 18 acyclic saturated hydrocarbon can comprise, can consist essentially of, or can be, a C 8 acyclic saturated hydrocarbon, a C 10 acyclic saturated hydrocarbon, a C 12 acyclic saturated hydrocarbon, a C 14 acyclic saturated hydrocarbon, or combinations thereof.
- the acyclic saturated hydrocarbons can comprise, can consist essentially of, or can be, octane, decane, dodecane, tetradecane, or combinations thereof; alternatively, decane, dodecane, or combinations thereof; alternatively, octane; alternatively, decane; alternatively, dodecane; or alternatively, tetradecane.
- the acyclic saturated hydrocarbons can comprise, can consist essentially of, or can be, decane, dodecane, or combinations thereof; alternatively, decane; or alternatively, dodecane.
- the saturated hydrocarbons can comprise, can consist essentially of, or can be, acyclic saturated hydrocarbons.
- the first compositions disclosed herein can further comprise from 0.2 mol% to 6 mol%, from 0.3 mol% to 4 mol%, from 0.4 mol% to 2 mol%, or from 0.5 mol% to 1.5 mol% acyclic saturated hydrocarbons.
- the acyclic saturated hydrocarbons can comprise from 10 mol% to 26 mol%, from 12 mol% to 24 mol%, or from 14 mol% to 22 mol% octane.
- the acyclic saturated hydrocarbons can comprise from 24 mol% to 48 mol%, from 27 mol% to 45 mol%, or from 30 mol% to 42 mol% decane. In an embodiment, the acyclic saturated hydrocarbons can comprise from 22 mol% to 40 mol%, from 24 mol% to 38 mol%, or from 26 mol% to 36 mol% dodecane. In an embodiment, the acyclic saturated hydrocarbons can comprise from 7 mol% to 23 mol%, from 9 mol% to 21 mol%, or from 11 mol% to 19 mol% tetradecane.
- the acyclic saturated hydrocarbons can comprise a) from 10 mol% to 26 mol%, from 12 mol% to 24 mol%, or from 14 mol% to 22 mol% octane; b) from 24 mol% to 48 mol%, from 27 mol% to 45 mol%, or from 30 mol% to 42 mol% decane; c) from 22 mol% to 40 mol%, from 24 mol% to 38 mol%, or from 26 mol% to 36 mol% dodecane; and d) from 7 mol% to 23 mol%, from 9 mol% to 21 mol%, or from 11 mol% to 19 mol% tetradecane.
- the saturated hydrocarbons can comprise, can consist essentially of, or can be, a cyclic saturated hydrocarbon.
- the first compositions disclosed herein can further comprise from 1.9 mol% to 5.1 mol%, from 2.1 mol% to 4.9 mol%, from 2.3 mol% to 4.7 mol%, or from 2.5 mol% to 4.5 mol% cyclic saturated hydrocarbons.
- the saturated hydrocarbons can comprise, can consist essentially of, or can be, a C 5 to C 8 cyclic saturated hydrocarbon.
- the C 5 to C 8 cyclic saturated hydrocarbon can comprise, can consist essentially of, or can be, a C 5 cyclic saturated hydrocarbon, a C 6 cyclic saturated hydrocarbon, a C 7 cyclic saturated hydrocarbon, a C 8 cyclic saturated hydrocarbon, or combinations thereof; alternatively, a C 5 cyclic saturated hydrocarbon; alternatively, a C 6 cyclic saturated hydrocarbon; alternatively, a C 7 cyclic saturated hydrocarbon; or alternatively, a C 8 cyclic saturated hydrocarbon.
- the C 5 to C 8 cyclic saturated hydrocarbon can comprise, can consist essentially of, or can be, a C 6 cyclic saturated hydrocarbon, a C 7 cyclic saturated hydrocarbon, or combinations thereof.
- the cyclic saturated hydrocarbons can comprise, can consist essentially of, or can be, methylcyclopentane, cyclohexane, methylcyclohexane, or combinations thereof; alternatively, methylcyclopentane; alternatively, cyclohexane; or alternatively, methylcyclohexane.
- the first composition can comprise an aromatic hydrocarbon.
- the first compositions disclosed herein can further comprise from 1 mol% to 3.4 mol%, from 1.2 mol% to 3.2 mol%, from 1.4 mol% to 3.0 mol%, or from 1.6 mol% to 2.8 mol% of an aromatic hydrocarbon.
- the first compositions disclosed herein can further comprise a C 6 to C 12 aromatic hydrocarbon or C 6 to C 12 aromatic compound.
- the C 6 to C 12 aromatic hydrocarbon can comprise, can consist essentially of, or can be, a C 6 aromatic hydrocarbon, a C 7 aromatic hydrocarbon, a C 8 aromatic hydrocarbon, a C 9 aromatic hydrocarbon, a C 10 aromatic hydrocarbon, a C 11 aromatic hydrocarbon, a C 12 aromatic hydrocarbon, or combinations thereof; alternatively, a C 6 aromatic hydrocarbon, a C 7 aromatic hydrocarbon, a C 8 aromatic hydrocarbon, or combinations thereof; alternatively, a C 6 aromatic hydrocarbon; alternatively, a C 7 aromatic hydrocarbon; alternatively, a C 8 aromatic hydrocarbon; alternatively, a C 9 aromatic hydrocarbon; alternatively, a C 10 aromatic hydrocarbon; alternatively, a C 11 aromatic hydrocarbon; or alternatively, a C 12 aromatic hydrocarbon.
- the C 6 to C 12 aromatic hydrocarbon can comprise, can consist essentially of, or can be, a C 6 aromatic hydrocarbon, a C 7 aromatic hydrocarbon, a C 8 aromatic hydrocarbon, or combinations thereof; alternatively, a C 6 aromatic hydrocarbon; alternatively, a C 7 aromatic hydrocarbon; or alternatively, a C 8 aromatic hydrocarbon.
- the C 6 to C 12 aromatic hydrocarbon can comprise, can consist essentially of, or can be, benzene, toluene, ethylbenzene, xylene, mesitylene, hexamethylbenzene, or combination thereof; alternatively, benzene, toluene, ethylbenzene, xylene, mesitylene, or combinations thereof; alternatively, toluene, ethylbenzene, xylene, or combinations thereof; alternatively, benzene; alternatively, toluene; alternatively, ethylbenzene; alternatively, xylene; alternatively, mesitylene; or alternatively, hexamethylbenzene.
- the first compositions disclosed herein can further comprise an alcohol.
- the first compositions disclosed herein can further comprise from 0.4 mol% to 3 mol%, from 0.6 mol% to 3 mol%, from 0.8 mol% to 2.5 mol%, or from 1 mol% to 2 mol% of an alcohol.
- the alcohol can comprise, can consist essentially of, or can be, a C 4 to C 12 alcohol; alternatively a C 6 to C 12 alcohol; or alternatively a C 6 to C 10 alcohol.
- the alcohol can comprise, can consist essentially of, or can be, a C 4 alcohol, a C 5 alcohol, a C 6 alcohol, a C 7 alcohol, a C 8 alcohol, a C 9 alcohol, a C 10 alcohol, a C 11 alcohol, a C 12 alcohol, or combinations thereof; alternatively, a C 6 alcohol, a C 7 alcohol, a C 8 alcohol, a C 9 alcohol, a C 10 alcohol, a C 11 alcohol, a C 12 alcohol, or combinations thereof; alternatively, a C 6 alcohol, a C 7 alcohol, a C 8 alcohol, a C 9 alcohol, a C 10 alcohol, or combinations thereof; alternatively, a C 4 alcohol; alternatively, a C 5 alcohol; alternatively, a C 6 alcohol; alternatively, a C 7 alcohol; alternatively, a C 8 alcohol; alternatively, a C 9 alcohol; alternatively, a C 10 alcohol; alternatively, a C 11 alcohol; or alternatively, a C 12 alcohol.
- the alcohol can comprise, can consist essentially of, or can be, 1-hexanol, 2-hexanol, 3-hexanol, 1-heptanol, 2-heptanol, 3-heptanol, 4-heptanol, 2-ethyl-1-hexanol, 2-methyl-3-heptanol, 1-octanol, 2-octanol, 3-octanol, 4-octanol, 1-decanol, 2-decanol, 3-decanol, 4-decanol, 5-decanol, 7-methyl-2-decanol, 2-ethyl-1-decanol, or combinations thereof; alternatively, 1-hexanol, 2-hexanol, 3-hexanol, 1-heptanol, 2-heptanol, 3-heptanol, 4-heptanol, 2-ethyl-1-hexanol, 2-methyl-3-heptanol, 1-
- the second compositions disclosed herein can comprises less than 3 mol%, less than 2.5 mol%, less than 2 mol%, less than 1.5 mol%, less than 1 mol%, or less than 0.5 mol% C 9- hydrocarbons.
- the C 9- hydrocarbons that can be present in the second compositions disclosed herein can comprise, can consist essentially of, or can be saturated C 9- hydrocarbons (acyclic and/or cyclic), C 9- monoolefins, or combinations thereof; alternatively, saturated C 9- hydrocarbons (acyclic and/or cyclic); or alternatively, C 9- monoolefins.
- the C 9- monoolefins that can be present in the second compositions disclosed herein can comprise, can consist essentially of, or can be, a C 7 monoolefin, a C 8 monoolefin, a C 9 monoolefin, or combinations thereof; alternatively, a C 7 monoolefin; alternatively, a C 8 monoolefin; or alternatively, a C 9 monoolefin.
- the C 9- monoolefins that can be present in the second compositions disclosed herein can comprise, can consist essentially of, or can be, a C 8 monoolefin.
- the C 9- monoolefins that can be present in the second compositions disclosed herein can comprise, can consist essentially of, or can be, 1-octene.
- the C 9- saturated hydrocarbons that can be present in the second compositions disclosed herein can comprise, can consist essentially of, or can be C 9- acyclic saturated hydrocarbons, C 9- cyclic saturated hydrocarbons, or combinations thereof; alternatively, C 9- acyclic saturated hydrocarbons; or alternatively, C 9- cyclic saturated hydrocarbons.
- the C 9- acyclic saturated hydrocarbons that can be present in the second compositions disclosed herein can comprise, can consist essentially of, or can be, a C 7 acyclic saturated hydrocarbon, a C 8 acyclic saturated hydrocarbon, a C 9 acyclic saturated hydrocarbon, or combinations thereof; alternatively, a C 7 acyclic saturated hydrocarbon; alternatively, a C 8 acyclic saturated hydrocarbon; or alternatively, a C 9 acyclic saturated hydrocarbon.
- the C 9- cyclic saturated hydrocarbon that can be present in the second compositions disclosed herein can comprise, can consist essentially of, or can be, a C 6 cyclic saturated hydrocarbon, a C 7 cyclic saturated hydrocarbon, a C 8 cyclic saturated hydrocarbon, a C 9 cyclic saturated hydrocarbon, or combinations thereof; a C 6 cyclic saturated hydrocarbon; alternatively, a C 7 cyclic saturated hydrocarbon; alternatively, a C 8 cyclic saturated hydrocarbon; or alternatively, a C 8 cyclic saturated hydrocarbon.
- the C 9- cyclic saturated hydrocarbons that can be present in the second compositions disclosed herein can comprise, can consist essentially of, or can be, methylcyclopentane, cyclohexane, methylcyclohexane, or combinations thereof; alternatively, methylcyclopentane; alternatively, cyclohexane; or alternatively, methylcyclohexane.
- the second compositions disclosed herein can comprise less than 1 mol%, less than 0.75 mol%, less than 0.5 mol%, less than 0.25 mol%, less than 0.1 mol%, less than 0.05 mol%, less than 0.25 mol%, or less than 0.01 mol% of a C 6 to C 12 aromatic hydrocarbon.
- the aromatic hydrocarbons that can be present in the second compositions disclosed herein can comprise, can consist essentially of, or can be, benzene, toluene, ethylbenzene, xylene, mesitylene, or combination thereof; alternatively, benzene, toluene, ethylbenzene, xylene, mesitylene, or combinations thereof; alternatively, toluene, ethylbenzene, xylene, or combinations thereof; alternatively, benzene; alternatively, toluene; alternatively, ethylbenzene; alternatively, xylene; or alternatively, mesitylene.
- the second compositions disclosed herein can comprise less than 1 mol%, less than 0.75 mol%, less than 0.5 mol%, less than 0.25 mol%, less than 0.1 mol%, less than 0.05 mol%, less than 0.25 mol%, or less than 0.01 mol% alcohol.
- the alcohols that can be present in the second compositions disclosed herein can comprise, can consist essentially of, or can be, 1-hexanol, 2-hexanol, 3-hexanol, 1-heptanol, 2-heptanol, 3-heptanol, 4-heptanol, 2-ethyl-1-hexanol, 2-methyl-3-heptanol, 1-octanol, 2-octanol, 3-octanol, 4-octanol, or combinations thereof; alternatively, 1-hexanol; alternatively, 2-hexanol; alternatively, 3-hexanol; alternatively, 1-heptanol; alternatively, 2-heptanol; alternatively, 3-heptanol; alternatively, 4-heptanol; alternatively, 2-ethyl-1-hexanol; alternatively, 2-methyl-3-heptanol; alternatively, 1-octanol; alternatively, 2-o
- the alcohols that can be present in the second compositions disclosed herein can comprise, can consist essentially of, or can be, 1-hexanol, 2-hexanol, 3-hexanol, or combinations thereof; alternatively, 1-hexanol; alternatively, 2-hexanol; or alternatively, 3-hexanol.
- the second compositions disclosed herein can comprises less than 3 mol%, less than 2.5 mol%, less than 2 mol%, less than 1.5 mol%, less than 1 mol%, or less than 0.5 mol% C 11+ hydrocarbons.
- the C 11+ hydrocarbons that can be present in the second compositions disclosed herein can comprise, can consist essentially of, or can be saturated C 11+ hydrocarbons (acyclic and/or cyclic), C 11+ monoolefins, or combinations thereof; alternatively, saturated C 11+ hydrocarbons (acyclic and/or cyclic); or alternatively, C 11+ monoolefins.
- the C 11+ monoolefin that can be present in the second compositions disclosed herein can comprise, can consist essentially of, or can be, a C 11 monoolefin, a C 12 monoolefin, a C 13 monoolefin, or combinations thereof; alternatively, a C 11 monoolefin; alternatively, a C 12 monoolefin; or alternatively, a C 13 monoolefin.
- the C 11+ acyclic saturated hydrocarbon that can be present in the second compositions disclosed herein can comprise, can consist essentially of, or can be, a C 11 acyclic saturated hydrocarbon, a C 12 acyclic saturated hydrocarbon, a C 13 acyclic saturated hydrocarbon, or combinations thereof; alternatively, a C 11 acyclic saturated hydrocarbon; alternatively, a C 12 acyclic saturated hydrocarbon; or alternatively, a C 13 acyclic saturated hydrocarbon.
- the C 11+ acyclic saturated hydrocarbon that can be present in the second compositions can comprise, can consist essentially of, or can be, dodecane.
- compositions disclosed herein can be prepared by a process comprising a) contacting 1) ethylene, 2) a catalyst system comprising i) a chromium containing compound, ii) a heteroatomic ligand, and iii) an alkylaluminum compound, and 3) optionally a reaction system diluent; b) forming an oligomer product comprising 1-hexene and/or 1-octene in a reaction system; c) discharging a reaction system effluent from the reaction system; d) contacting the reaction system effluent with a catalyst system deactivating agent; and e) isolating the composition.
- the process can comprise a) contacting 1) ethylene, 2) a catalyst system comprising i) a chromium containing compound, ii) a heteroatomic ligand, and iii) an alkylaluminum compound, and 3) optionally a reaction system diluent; b) forming an oligomer product comprising 1-hexene and/or 1-octene in a reaction system; c) discharging a reaction system effluent from the reaction system; d) contacting the reaction system effluent with a catalyst system deactivating agent; and e) isolating a composition comprising (a) at least 76 mol%, at least 78 mol%, at least 80 mol%, or at least 82 mol% C 10 monoolefins, the C 10 monoolefins comprising (i) at least 3 mol%, at least 4 mol%, at least 5 mol%, at least 6 mol%, at least 7 mol
- the process can comprise a) contacting 1) ethylene, 2) a catalyst system comprising i) a chromium containing compound, ii) a heteroatomic ligand, and iii) an alkylaluminum compound, and 3) optionally a reaction system diluent; b) forming an oligomer product comprising 1-hexene and/or 1-octene in a reaction system; c) discharging a reaction system effluent from the reaction system; d) contacting the reaction system effluent with a catalyst system deactivating agent; and e) isolating a composition comprising at least 95 mol%, at least 96 mol%, at least 97 mol%, at least 98 mol%, or at least 99 mol% C 10 monoolefins, the C 10 monoolefins comprising (i) at least 3 mol%, at least 4 mol%, at least 5 mol%, at least 6 mol%, or
- the process can comprise a) contacting 1) ethylene, 2) a catalyst system comprising i) a chromium containing compound, ii) a heteroatomic ligand, and iii) an alkylaluminum compound, and 3) optionally a reaction system diluent; b) forming an oligomer product comprising 1-hexene and/or 1-octene in a reaction system, c) discharging a reaction system effluent from the reaction system; d) contacting the reaction system effluent with a catalyst system deactivating agent; e) isolating a first composition comprising (a) at least 76 mol%, at least 78 mol%, at least 80 mol%, or at least 82 mol% C 10 monoolefins, the C 10 monoolefins comprising (i) at least 3 mol%, at least 4 mol%, at least 5 mol%, at least 6 mol%, at least 7
- reaction system refers to a portion of a process, associated equipment and associated process lines where all necessary reaction components and reaction conditions are present such that a reaction (e.g., oligomerization reaction, ethylene oligomerization, ethylene trimerization, ethylene tetramerization, etc.) can occur at a desired rate.
- a reaction e.g., oligomerization reaction, ethylene oligomerization, ethylene trimerization, ethylene tetramerization, etc.
- the reaction system begins where the necessary reaction components and reaction conditions are present to maintain a reaction within 25% of an average reaction rate (e.g., reaction rate is greater than or equal to 25% of the average reaction rate) and the reaction system ends where the conditions do not maintain a reaction rate within 25% of the average reaction rate (e.g., reaction rate is less than 25% of the average reaction rate), based upon a volume average of the reaction rate of the reaction system).
- an average reaction rate e.g., reaction rate is greater than or equal to 25% of the average reaction rate
- the reaction system ends where the conditions do not maintain a reaction rate within 25% of the average reaction rate (e.g., reaction rate is less than 25% of the average reaction rate), based upon a volume average of the reaction rate of the reaction system).
- the reaction system begins at the point where sufficient ethylene and catalyst system (e.g., active catalyst system) is present under sufficient reaction conditions to maintain oligomer product production at a desired rate and the reaction system ends at a point where either the catalyst system is deactivated, sufficient ethylene is not present to sustain oligomer product production, or other reaction conditions are not sufficient to maintain the oligomer product production and/or a desired oligomer product production rate.
- catalyst system e.g., active catalyst system
- the reaction system can comprise one or more reactor systems, one or more reactors, and/or associated equipment where all the necessary reaction components and reaction conditions are present such that the reaction can occur at a desired rate.
- compositions disclosed herein can be isolated from an ethylene trimerization process comprising contacting ethylene and any ethylene trimerization catalyst system disclosed herein to form a trimerization product (or oligomer product) comprising 1-hexene.
- compositions disclosed herein can be isolated from an ethylene tetramerization process comprising contacting ethylene and any ethylene tetramerization catalyst system disclosed herein to form a tetramerization product (or oligomer product) comprising 1-octene.
- compositions disclosed herein can be isolated from an ethylene trimerization and tetramerization process comprising contacting ethylene and any ethylene trimerization and tetramerization catalyst system disclosed herein to form a trimerization and tetramerization product (or oligomer product) comprising 1-hexene and 1-octene.
- trimerization catalyst system, tetramerization catalyst system, and trimerization and tetramerization catalyst system are independently described herein and these features can be utilized without limitation to further describe the processes described herein which can produce the compositions disclosed herein.
- ethylene trimerization, ethylene tetramerization, or ethylene trimerization and tetramerization can be performed in the presence of a solvent.
- ethylene trimerization, ethylene tetramerization, or ethylene trimerization and tetramerization can comprise contacting hydrogen with ethylene and the catalyst system.
- the process can further comprise recovering the trimer, tetramer, or trimer and tetramer.
- ethylene, the catalyst system (or components of the catalyst system), reaction system solvent (if utilized), hydrogen (if utilized), and any other materials can be a fed to the reaction system and can be supplied to the reaction system via one or more feed lines.
- ethylene trimerization mixture refers to a mixture (e.g., reaction mixture) comprising ethylene, the catalyst system (or components of the catalyst system), reaction system solvent (if utilized), hydrogen (if utilized), and any other materials necessary for the oligomerization process.
- the ethylene trimerization mixture, ethylene tetramerization mixture, or ethylene trimerization and tetramerization mixture can comprise at least 0.1 wt.%, at least 0.5 wt.%, at least 1 wt.%, at least 2.5 wt.%, at least 5 wt.%, at least 7.5 wt.%, or at least 10 wt.% ethylene, based upon the ethylene trimerization, tetramerization, or trimerization and tetramerization mixture.
- the ethylene trimerization mixture, ethylene tetramerization mixture, or ethylene trimerization and tetramerization mixture can comprise a maximum of 50 wt.%, 40 wt.%, 30 wt.%, 25 wt.%, 20 wt.%, 17.5 wt.%, or 15 wt.% ethylene, based upon the trimerization, tetramerization, or trimerization and tetramerization mixture.
- the ethylene in the ethylene trimerization mixture, ethylene tetramerization mixture, or ethylene trimerization and tetramerization mixture can range from any minimum weight percent disclosed herein to any maximum weight percent disclosed herein.
- the ethylene in the ethylene trimerization mixture, ethylene tetramerization mixture, or ethylene trimerization and tetramerization mixture can range from 0.1 wt.% to 50 wt.%, from 5 wt.% to 40 wt.%, from 5 wt.% to 30 wt.%, from 10 wt.% to 30 wt.%, from 10 wt.% to 25 wt.%, from 10 wt.% to 20 wt.%, from 10 wt.% to 15 wt.%, or combinations thereof.
- any other suitable ranges for the amount of ethylene that can be present in the ethylene trimerization mixture, ethylene tetramerization mixture, or ethylene trimerization and tetramerization mixture can be used.
- the process (e.g., ethylene oligomerization process) can be an ethylene trimerization process, ethylene tetramerization process, or an ethylene trimerization and tetramerization process comprising contacting 1) ethylene and 2) a catalyst system comprising i) a chromium containing compound, ii) a heteroatomic ligand, and iii) an alkylaluminum compound to form an ethylene trimerization product, an ethylene tetramerization product, or an ethylene trimerization and tetramerization product (respectively).
- a catalyst system comprising i) a chromium containing compound, ii) a heteroatomic ligand, and iii) an alkylaluminum compound to form an ethylene trimerization product, an ethylene tetramerization product, or an ethylene trimerization and tetramerization product (respectively).
- the process can be an ethylene trimerization process, ethylene tetramerization process, or an ethylene trimerization and tetramerization process, comprising contacting 1) ethylene and 2) a catalyst system comprising i) a chromium containing compound complexed to a heteroatomic ligand, and ii) an alkylaluminum compound to form an ethylene trimerization product, an ethylene tetramerization product, or an ethylene trimerization and tetramerization product (respectively).
- an optional halogen containing compound can be a component of the catalyst system, or alternatively, a halogen containing compound can be a further component of the ethylene trimerization mixture, ethylene tetramerization mixture, or ethylene trimerization and tetramerization mixture contacted to form an ethylene trimerization product, an ethylene tetramerization product, or an ethylene trimerization and tetramerization product.
- a solvent e.g., reaction system diluent
- a solvent can be a further component of the ethylene trimerization mixture, ethylene tetramerization mixture, or ethylene trimerization and tetramerization mixture contacted to form an ethylene trimerization product, an ethylene tetramerization product, or an ethylene trimerization and tetramerization product.
- hydrogen can be a further component of the ethylene trimerization mixture, ethylene tetramerization mixture, or ethylene trimerization and tetramerization mixture contacted to form an ethylene trimerization product, an ethylene tetramerization product, or an ethylene trimerization and tetramerization product.
- the process (e.g., ethylene oligomerization process, ethylene trimerization process, ethylene tetramerization process, or ethylene trimerization and tetramerization process) can include steps for forming an oligomer product in a reaction system (as described herein), discharging a reaction system effluent from the reaction system (as described herein), contacting the reaction system effluent with a catalyst system deactivating agent (as described herein), and/or isolating a composition (e.g., the first composition and/or second composition).
- a reaction system as described herein
- discharging a reaction system effluent from the reaction system as described herein
- a catalyst system deactivating agent as described herein
- isolating a composition e.g., the first composition and/or second composition.
- an ethylene trimerization process, an ethylene tetramerization process, or an ethylene trimerization and tetramerization process can utilize a solvent.
- solvent can be a hydrocarbon, a halogenated hydrocarbon, or combinations thereof.
- Hydrocarbons and halogenated hydrocarbons which can be used as solvent can include, for example, aliphatic hydrocarbons, aromatic hydrocarbons, petroleum distillates, halogenated aliphatic hydrocarbons, halogenated aromatic hydrocarbons, or combinations thereof.
- Aliphatic hydrocarbons which can be used as a solvent include C 3 to C 20 aliphatic hydrocarbons, alternatively, C 4 to C 15 aliphatic hydrocarbons, or alternatively, C 5 to C 10 aliphatic hydrocarbons, for example.
- the aliphatic hydrocarbons which can be used as a solvent can be cyclic or acyclic and/or can be linear or branched, unless otherwise specified.
- Non-limiting examples of suitable acyclic aliphatic hydrocarbon solvents that can be utilized singularly or in any combination include propane, iso-butane, n-butane, butane (n-butane or a mixture of linear and branched C 4 acyclic aliphatic hydrocarbons), pentane (n-pentane or a mixture of linear and branched C 5 acyclic aliphatic hydrocarbons), hexane (n-hexane or mixture of linear and branched C 6 acyclic aliphatic hydrocarbons), heptane (n-heptane or a mixture of linear and branched C 7 acyclic aliphatic hydrocarbons), octane (n-octane or a mixture of linear and branched C 8 acyclic aliphatic hydrocarbons), or combinations thereof.
- Non-limiting examples of suitable cyclic aliphatic hydrocarbon which can be used as a solvent include cyclohexane, methyl cyclohexane, or combinations thereof.
- Aromatic hydrocarbons which can be used as a solvent include aromatic hydrocarbons, or C 6 to C 10 aromatic hydrocarbons.
- suitable aromatic hydrocarbons that can be utilized singularly or in any combination as a solvent include benzene, toluene, xylene (including ortho-xylene, meta-xylene, para-xylene, or mixtures thereof), ethylbenzene, or combinations thereof.
- Halogenated aliphatic hydrocarbons which can be used as a solvent include C 1 to C 15 halogenated aliphatic hydrocarbons, alternatively, C 1 to C 10 halogenated aliphatic hydrocarbons, or alternatively, C 1 to C 5 halogenated aliphatic hydrocarbons, for example.
- the halogenated aliphatic hydrocarbons which can be used as a solvent can be cyclic or acyclic and/or can be linear or branched, unless otherwise specified.
- suitable halogenated aliphatic hydrocarbons which can be used as a solvent include methylene chloride, chloroform, carbon tetrachloride, dichloroethane, trichloroethane, or combinations thereof.
- Halogenated aromatic hydrocarbons which can be useful as a solvent include C 6 to C 20 halogenated aromatic hydrocarbons, or alternatively, C 6 to C 10 halogenated aromatic hydrocarbons, for example.
- suitable halogenated aromatic hydrocarbons which can be used as a solvent include chlorobenzene, dichlorobenzene, or combinations thereof, for example.
- the choice of solvent can be made on a basis of convenience in processing.
- isobutane can be chosen to be compatible with diluents used for formation of polyolefins in a subsequent processing step.
- the solvent can be chosen to be easily separable from the trimer, tetramer, or trimer and tetramer.
- a component of the trimerization, tetramerization, or trimerization and tetramerization product or feedstock can be utilized as the solvent.
- 1-hexene can be a component of the trimerization product of an ethylene trimerization process, it can be chosen as the solvent to decrease the need for separation.
- a process can be carried out in a solvent which is a product of the ethylene trimerization, tetramerization, or trimerization and tetramerization process. Therefore, the choice of reaction system diluent, or solvent, can be based on the selection of the initial olefin reactant (e.g., ethylene) and/or the trimerization, tetramerization, or trimerization and tetramerization product. For example, if the catalyst system is used to trimerize ethylene to 1-hexene, the solvent for the trimerization reaction can be 1-hexene.
- the reaction mixture e.g., ethylene trimerization mixture, ethylene tetramerization mixture, or ethylene trimerization and tetramerization mixture
- the reaction mixture can further comprise a catalyst system (e.g., oligomerization catalyst system, ethylene trimerization catalyst system, ethylene tetramerization catalyst system, or ethylene trimerization and tetramerization catalyst system), or one or more components thereof.
- a catalyst system e.g., oligomerization catalyst system, ethylene trimerization catalyst system, ethylene tetramerization catalyst system, or ethylene trimerization and tetramerization catalyst system
- the ethylene trimerization catalyst system, ethylene tetramerization catalyst system, or ethylene trimerization and tetramerization catalyst system can comprise a chromium containing compound, a heteroatomic ligand, and a metal alkyl compound (or alternatively, an alkylaluminum compound).
- the ethylene trimerization catalyst system, ethylene tetramerization catalyst system, or ethylene trimerization and tetramerization catalyst system can comprise a chromium containing compound complexed to a heteroatomic ligand, and a metal alkyl compound (or alternatively, an alkylaluminum compound).
- the ethylene trimerization catalyst system, ethylene tetramerization catalyst system, or ethylene trimerization and tetramerization catalyst system can further comprise a halogen containing compound.
- the chromium containing compound, chromium containing compound complexed to a heteroatomic ligand, heteroatomic ligand, metal alkyl compound (or alternatively, alkylaluminum compound), and optional halogen containing compound are each independent elements of the catalyst system.
- the chromium containing compound (of the catalyst systems disclosed herein) can have a chromium oxidation state of from 0 to 6, or from 2 to 3 (i.e., a chromium(II) compound or a chromium(III) compound).
- chromium(II) compounds which can be used in the catalyst system disclosed herein can include chromium(II) nitrate, chromium(II) sulfate, chromium(II) fluoride, chromium(II) chloride, chromium(II) bromide, or chromium(II) iodide.
- Non-limiting examples of chromium(III) compounds which can be used in the catalyst systems disclosed herein can include chromium(III) nitrate, chromium(III) sulfate, chromium(III) fluoride, chromium(III) chloride, chromium(III) bromide, or chromium(III) iodide.
- the catalyst system can comprise a chromium(II) alkoxide, a chromium(II) carboxylate, a chromium(II) beta-dionate, a chromium(III) alkoxide, a chromium(III) carboxylate, or a chromium(III) beta-dionate.
- each carboxylate group of the chromium containing compound independently can be a C 2 to C 24 carboxylate group, alternatively, a C 4 to C 19 carboxylate group, or alternatively, a C 5 to C 12 carboxylate group.
- each alkoxy group of the chromium containing compound independently can be a C 1 to C 24 alkoxy group, alternatively, a C 4 to C 19 alkoxy group, or alternatively, a C 8 to C 12 alkoxy group.
- each aryloxy group of the chromium containing compound independently can be a C 6 to C 24 aryloxy group, alternatively, a C 6 to C 19 aryloxy group, or alternatively, a C 6 to C 12 aryloxy group.
- each beta-dionate group of the chromium containing compound independently can be a C 5 to C 24 beta-dionate group, alternatively, a C 5 to C 19 beta-dionate group, or alternatively, a C 5 to C 12 beta-dionate group.
- Chromium carboxylates can be particularly useful for the catalyst systems disclosed herein.
- the catalyst systems disclosed herein can comprise a chromium carboxylate comprising a C 2 to C 24 monocarboxylate, alternatively, a C 4 to C 19 monocarboxylate, or alternatively, a C 5 to C 12 monocarboxylate.
- each carboxylate group of the chromium carboxylate independently can be an acetate, a propionate, a butyrate, a pentanoate, a hexanoate, a heptanoate, an octanoate, a nonanoate, a decanoate, an undecanoate, a dodecanoate, a tridecanoate, a tetradecanoate, a pentadecanoate, a hexadecanoate, a heptadecanoate, or an octadecanoate; or alternatively, a pentanoate, a hexanoate, a heptanoate, an octanoate, a nonanoate, a decanoate, an undecanoate, or a dodecanoate.
- each carboxylate group of the chromium carboxylate independently can be acetate, propionate, n-butyrate, isobutyrate, valerate (n-pentanoate), neo-pentanoate, capronate (n-hexanoate), n-heptanoate, caprylate (n-octanoate), 2-ethylhexanoate, n-nonanoate, caprate (n-decanoate), n-undecanoate, laurate (n-dodecanoate), or stearate (n-octadecanoate); or alternatively, valerate (n-pentanoate), neo-pentanoate, capronate (n-hexanoate), n-heptanoate, caprylate (n-octanoate), 2-ethylhexanoate, n-nonanoate, caprate (
- the chromium containing compound can comprise, can consist essentially of, or can be, a chromium(II) carboxylate or a chromium(III) carboxylate.
- the chromium(II) carboxylates can comprise, can consist essentially of, or can be, chromium(II) acetate, chromium(II) propionate, chromium(II) butyrate, chromium(II) isobutyrate, chromium(II) neopentanoate, chromium(II) oxalate, chromium(II) octanoate, chromium(II) 2-ethylhexanoate, chromium(II) laurate, or chromium(II) stearate; or alternatively, chromium(II) acetate, chromium(II) propionate, chrom
- the chromium(III) carboxylates can comprise, can consist essentially of, or can be, chromium(III) acetate, chromium(III) propionate, chromium(III) butyrate, chromium(III) isobutyrate, chromium(III) neopentanoate, chromium(III) oxalate, chromium (III) octanoate, chromium(III) 2-ethylhexanoate, chromium(III) 2,2,6,6,-tetramethylheptanedionate, chromium(III) naphthenate, chromium(III) laurate, or chromium(III) stearate.
- the heteroatomic ligand (whether it is a separate component of the catalyst system or is a ligand complexed to the chromium containing compound of the catalyst system) can comprise, can consist essentially of, or can be, an amine compound, an amide compound, an imide compound, or combinations thereof.
- the heteroatomic ligand (whether it is a separate component of the catalyst system or is a ligand complexed to the chromium containing compound of the catalyst system) can comprise, can consist essentially of, or can be, a pyrrole compound, a diphosphino aminyl compound, an N 2 -phosphinyl amidine compound, an N 2 -phosphinyl formamidine compound, an N 2 -phosphinyl guanidine compound, or combinations thereof.
- the heteroatomic ligand (whether it is a separate component of the catalyst system or is a ligand complexed to the chromium containing compound of the catalyst system) can comprise, can consist essentially of, or can be, a pyrrole compound; alternatively, a diphosphino aminyl compound; alternatively, an N 2 -phosphinyl amidine compound; alternatively, an N 2 -phosphinyl formamidine compound; or alternatively, an N 2 -phosphinyl guanidine compound.
- the amine compound can be a C 2 to C 30 amine; alternatively, a C 2 to C 20 amine; alternatively, C 2 to C 15 amine; or alternatively, a C 2 to C 10 amine.
- the amide compound can be a C 3 to C 30 amide; alternatively, a C 3 to C 20 amide; alternatively, C 3 to C 15 amide; or alternatively, a C 3 to C 10 amide.
- the imide compound can be a C 4 to C 30 imide; alternatively, a C 4 to C 20 imide; alternatively, C 4 to C 15 imide; or alternatively, a C 4 to C 10 imide.
- the pyrrole compound which can be utilized in the catalyst systems disclosed herein can comprise any pyrrole compound that can form a chromium pyrrolide complex.
- the term "pyrrole compound” refers to pyrrole (C 5 H 5 N), derivatives of pyrrole (e.g., indole), substituted pyrroles, as well as metal pyrrolide compounds.
- a pyrrole compound is defined as a compound comprising a 5-membered, nitrogen-containing heterocycle, such as, for example, pyrrole, derivatives of pyrrole, or combinations thereof.
- the pyrrole compound can be pyrrole or any heteroleptic or homoleptic metal complex or salt containing a pyrrolide radical or ligand.
- the pyrrole compound can be a C 4 to C 30 pyrrole; alternatively, a C 4 to C 20 pyrrole; alternatively, C 4 to C 15 pyrrole; or alternatively, a C 4 to C 10 pyrrole.
- the pyrrole compound which can be utilized in the catalyst systems disclosed herein can have Formula PI or Formula 11. In an embodiment, the pyrrole compound which can be utilized in the catalyst systems disclosed herein can have Formula PI; or alternatively Formula 11.
- R 2p , R 3p , R 4p , and R 5p of Formula P1 and R 2i , R 3i , R 4i , R 5i , R 6i , and R 7i of Formula 11 can each independently be hydrogen, a C 1 to C 18 organyl group, or a C 3 to C 60 silyl group; alternatively, hydrogen, a C 1 to C 15 organyl group, or a C 3 to C 45 silyl group; alternatively, hydrogen, a C 1 to C 10 organyl group, or a C 3 to C 30 silyl group; alternatively, hydrogen, a C 1 to C 5 organyl group, or a C 3 to C 15 silyl group; alternatively, hydrogen, or a C 1 to C 18 organyl group; alternatively, hydrogen, or a C 1 to C 15 organyl group; alternatively, hydrogen, or a C 1 to C 10 organyl group; or alternatively, hydrogen, or a C 1 to C 5 organyl group.
- R 2p , R 3p , R 4p , and R 5p of Formula PI and R 2i , R 3i , R 4i , R 5i , R 6i , and R 7i of Formula 11 can each independently be hydrogen, a C 1 to C 18 hydrocarbyl group, or a C 3 to C 60 silyl group; alternatively, hydrogen, a C 1 to C 15 hydrocarbyl group, or a C 3 to C 45 silyl group; alternatively, hydrogen, a C 1 to C 10 hydrocarbyl group, or a C 3 to C 35 silyl group; alternatively, hydrogen, a C 1 to C 5 hydrocarbyl group, or a C 3 to C 15 silyl group; alternatively, hydrogen, or a C 1 to C 18 hydrocarbyl group; alternatively, hydrogen, or a C 1 to C 15 hydrocarbyl group; alternatively, hydrogen, or a C 1 to C 10 hydrocarbyl group; or alternatively, hydrogen, or a C 1 to C 1 to C
- the pyrrole compound which can be utilized in the catalyst systems disclosed herein can comprise, can consist essentially of, or can be, pyrrole, 2,5-dimethylpyrrole, 2-methyl-5-ethylpyrrole, 2-methyl-5-propylpyrrole, 2,5-diethylpyrrole, 3,4-dimethylpyrrole, 2,5-di-n-propylpyrrole, 2,5-di-n-butylpyrrole, 2,5-di-n-pentylpyrrole, 2,5-di-n-hexylpyrrole, 2,5-di-n-heptylpyrrole, 2,5-di-n-octylpyrrole, 2,5-dibenzylpyrrole, 2,4-dimethyl-3-ethylpyrrole, 2,3,5-triethylpyrrrole, 2,3,5-tri-n-butylpyrrrole, 2,3,5-tri-n-p
- pyrrole compounds that can be used in the catalyst system disclosed herein comprise, but are not limited to pyrrole-2-carboxylic acid, 2-acetylpyrrole, pyrrole-2-carboxaldehyde, tetrahydroindole, 2,5-dimethylpyrrole, 2,4-dimethyl-3-ethylpyrrole, 3-acetyl-2,4-dimethylpyrrole, ethyl-2,4-dimethyl-5-(ethoxycarbonyl)-3-pyrrole-propionate, ethyl-3,5-dimethyl-2-pyrrolecarboxylate, 3,4-dichloropyrrole, 2,3,4,5-tetrachloropyrrole, 2-acetylpyrrole, pyrazole, pyrrolidine, indole, dipyrrolylmethane, or combinations thereof.
- the pyrrole compound which can be utilized in the catalyst systems disclosed herein can comprise, can consist essentially of, or can be, pyrrole, 2,5-dimethylpyrrole, 2-methyl-5-ethylpyrrole, 2-methyl-5-propylpyrrole, 2,5-diethylpyrrole, or combinations thereof; alternatively, pyrrole; alternatively, 2,5-dimethylpyrrole; alternatively, 2-methyl-5-ethylpyrrole; alternatively, 2-methyl-5-propylpyrrole; or alternatively, 2,5-diethylpyrrole.
- the pyrrole compound which can be utilized in the catalyst systems disclosed herein can comprise a metal pyrrolide, such as an alkyl metal pyrrolide.
- the pyrrole compound which can be utilized in the catalyst systems disclosed herein can comprise, individually or in any combination, a dialkylaluminum pyrrolide of any pyrrole provided herein.
- Alkyl groups will be described in more detail later herein (e.g., as alkyl groups for the metal alkyl) and these alkyl groups can be utilized to further describe the alkyl metal pyrrolide and/or the dialkylaluminum pyrrolide which can be utilized as the pyrrole compound which can be utilized in the catalyst systems disclosed herein.
- the pyrrole compound which can be utilized in the catalyst systems disclosed herein can comprise diethylaluminum 2,5-dimethylpyrrolide, ethylaluminum di(2,5-dimethylpyrrolide), aluminum tri(2,5-dimethylpyrrolide), or combinations thereof.
- the heteroatomic ligand can be a diphosphino aminyl compound.
- a diphosphino aminyl compound is a compound having a moiety characterized by having a P-N-P (phosphorus-nitrogen-phosphorus) linkage.
- the moiety having the P-N-P linkage can hereafter be referred to as a "PNP moiety” or as a "diphosphino aminyl moiety.”
- the heteroatomic ligand comprising the diphosphino aminyl moiety can be referred to as a "PNP ligand," a "diphosphino aminyl ligand,” or a "diphosphino aminyl compound.”
- the heteroatomic ligand can comprise a diphosphino aminyl moiety having Structure PNP1: wherein R 1n , R 2n , R 3n , and R 4n can be any group described herein and the undesignated aminyl nitrogen valence ( ⁇ ) represents the remainder of the heteroatomic ligand.
- R 1n , R 2n , R 3n , and R 4n can each be different.
- R 1n , R 2n , R 3n , and R 4n can each be the same.
- R 1n and R 2n can be the same, and R 3n and R 4n can be the same, but different from R 1n and R 2n .
- R 1n and R 3n can be the same, and R 2n and R 4n can be the same, but different from R 1n and R 3n .
- R 1n , R 2n , R 3n , and/or R 4n of the diphosphino aminyl moiety independently can be a C 1 to C 30 alkyl group; alternatively, a C 1 to C 20 alkyl group; alternatively, a C 1 to C 15 alkyl group; alternatively, a C 1 to C 10 alkyl group; or alternatively, a C 1 to C 5 alkyl group.
- R 1n , R 2n , R 3n , and/or R 4n of the diphosphino aminyl moiety independently can be a C 6 to C 30 aromatic group; alternatively, a C 6 to C 20 aromatic group; alternatively, a C 6 to C 15 aromatic group; or alternatively, a C 6 to C 10 aromatic group.
- R 1n , R 2n , R 3n , and/or R 4n of the diphosphino aminyl moiety independently can be a phenyl group or a C 6 to C 30 substituted phenyl group; alternatively, a phenyl group or a C 6 to C 20 substituted phenyl group; alternatively, a phenyl group or a C 6 to C 15 substituted phenyl group; alternatively, a phenyl group or a C 6 to C 10 substituted phenyl group; or alternatively, a phenyl group.
- R 1n and R 2n , and/or R 3n and R 4n of the diphosphino aminyl moiety can be joined to form a ring (regardless of particular type of group - organyl, organyl consisting of inert functional groups, hydrocarbyl, or any species within) containing a phosphorus atom of the diphosphino aminyl moiety.
- General substituent groups are provided herein and these general substituent groups can be utilized to further describe the substituted phenyl groups which can be utilized as R 1n and R 2n , and/or R 3n and R 4n for the diphosphino aminyl moiety.
- R 1n , R 2n , R 3n , and R 4n independently can be an organyl group; alternatively, an organyl group comprising inert functional groups; or alternatively, a hydrocarbyl group.
- the organyl group which can be utilized as R 1n , R 2n , R 3n , and R 4n can be a C 1 to C 30 organyl group; alternatively, a C 1 to C 20 organyl group; alternatively, a C 1 to C 15 organyl group; alternatively, a C 1 to C 10 organyl group; or alternatively, a C 1 to C 5 organyl group.
- the organyl group comprising inert functional groups which can be utilized as R 1n , R 2n , R 3n , and R 4n can be a C 1 to C 30 organyl group comprising inert functional groups; alternatively, a C 1 to C 20 organyl group comprising inert functional groups; alternatively, a C 1 to C 15 organyl group comprising inert functional groups; alternatively, a C 1 to C 10 organyl group comprising inert functional groups; or alternatively, a C 1 to C 5 organyl group comprising inert functional groups.
- the hydrocarbyl group which can be utilized as R 1n , R 2n , R 3n , and R 4n can be a C 1 to C 30 hydrocarbyl group; alternatively, a C 1 to C 20 hydrocarbyl group; alternatively, a C 1 to C 15 hydrocarbyl group; alternatively, a C 1 to C 10 hydrocarbyl group; or alternatively, a C 1 to C 5 hydrocarbyl group.
- two or more of R 1n , R 2n , R 3n , and R 4n can be joined to form a ring or a ring system.
- the heteroatomic ligand can be a compound having an N 2 -phosphinyl formamidine group.
- a formamidine group has the general structure within the formamidine group, the nitrogen participating in a double bond with the central carbon atom is referred to as the N 1 nitrogen atom and the nitrogen atom participating in a single bond with the central carbon atom is referred to as the N 2 nitrogen atom.
- the groups attached to the N 1 and N 2 nitrogen atoms are referred to as the N 1 group and N 2 group, respectively.
- N 2 -phosphinyl formamidine group has the general structure within the N 2 -phosphinyl formamidine group, the N 1 and N 2 nitrogen atoms and the N 1 and N 2 groups have the same meaning as described for the formamidine group. Consequently, an N 2 -phosphinyl formamidine group has the phosphinyl group attached to the N 2 nitrogen atom.
- the heteroatomic ligand can be an N 2 -phosphinyl formamidine compound having Structure NPF1.
- a chromium containing compound complexed to an N 2 -phosphinyl formamidine compound can have Structure NPFCr1.
- R 1 , R 3 , R 4 , and R 5 within the N 2 -phosphinyl formamidine compound having Structure NPF1 and an N 2 -phosphinyl formamidine chromium complex (e.g., a chromium containing compound complexed to an N 2 -phosphinyl formamidine compound) having Structure NPFCr1 are independently described herein and can be utilized without limitation to further describe the N 2 -phosphinyl formamidine compound having Structure NPF1 and the N 2 -phosphinyl formamidine chromium complex having Structure NPFCr1.
- CrX p represents the chromium containing compound of the N 2 -phosphinyl formamidine chromium complex having Structure NPFCr1.
- Q represents an optional neutral ligand within the N 2 -phosphinyl formamidine chromium complex having Structure NPFCr1, while q represents the number of optional neutral ligands present.
- CrX p , Q, and q are independently described herein and can be utilized without limitation to further describe the N 2 -phosphinyl formamidine chromium complex having Structure NPFCr1. Additionally, CrX p , Q, and q can be combined with the independently described R 1 , R 3 , R 4 , and R 5 to further describe the N 2 -phosphinyl formamidine chromium complex having Structure NPFCr1.
- the heteroatomic ligand can be a compound having an N 2 -phosphinyl amidine group.
- an amidine group has the general structure within the amidine group, the nitrogen participating in a double bond with the central carbon atom is referred to as the N 1 nitrogen atom and the nitrogen atom participating in a single bond with the central carbon atom is referred to as the N 2 nitrogen atom.
- the groups attached to the N 1 and N 2 nitrogen atoms are referred to as the N 1 group and N 2 group, respectively.
- N 2 -phosphinyl amidine group has the general structure within the N 2 -phosphinyl amidine group, the N 1 and N 2 nitrogen atoms and the N 1 and N 2 groups have the same meaning as described for the amidine group. Consequently, an N 2 -phosphinyl amidine group has the phosphinyl group attached to the N 2 nitrogen atom. Within the amidine group and N 2 -phosphinyl amidine group, the carbon atom between the two nitrogen atoms is the central carbon atom and any substituent attached to it is referred to as the central carbon group.
- a compound having a pyridine group with a 2-amine group (or its analogues - e.g., a pyrimidine ring, an imidazole ring, a compound having 2-aminopyridine group, and the like) or having a 2-phosphinylamine group is not considered to constitute an amidine group or N 2 -phosphinyl amidine group, respectively.
- the heteroatomic ligand (whether it is a separate component of the catalyst system or is a ligand complexed to the transition metal compound of the catalyst system) can be an N 2 -phosphinyl amidine compound having Structure NPA1.
- the chromium containing compound complexed to an N 2 -phosphinyl amidine compound can have Structure NPACr1.
- R 1 , R 2 , R 3 , R 4 , and R 5 within the N 2 -phosphinyl amidine compound having Structure NPA1 and an N 2 -phosphinyl amidine chromium complex (e.g., a chromium containing compound complexed to an N 2 -phosphinyl amidine compound) having Structure NPACr1 are independently described herein and can be utilized without limitation to further describe the N 2 -phosphinyl amidine compound having Structure NPA1 and the N 2 -phosphinyl amidine chromium complex having Structure NPACr1.
- CrX p represents the chromium containing compound of the N 2 -phosphinyl amidine chromium complex having Structure NPACr1.
- Q represents an optional neutral ligand of the N 2 -phosphinyl amidine chromium complex having Structure NPACr1, while q represents the number of optional neutral ligands present.
- CrX p , Q, and q are independently described herein and can be utilized without limitation to further describe the N 2 -phosphinyl amidine chromium complex having Structure NPACr1. Additionally, CrX p , Q, and q can be combined with the independently described R 1 , R 2 , R 3 , R 4 , and R 5 to further describe the N 2 -phosphinyl amidine chromium complex having Structure NPACr1.
- the heteroatomic ligand can be a compound having an N 2 -phosphinyl guanidine group.
- a guanidine group has the general structure within the guanidine core, the nitrogen participating in a double bond with the central carbon atom is referred to as the N 1 nitrogen atom and the two nitrogen atoms participating in a single bond with the central carbon atom are referred to as the N 2 nitrogen atom and the N 3 nitrogen atom.
- the groups attached to the N 1 , N 2 and N 3 nitrogen atoms are referred to as the N 1 group, N 2 group, and N 3 group, respectively.
- N 2 -phosphinyl guanidine group such as those found in a ligand of the N 2 -phosphinyl guanidine complexes described herein, has the general structure within an N 2 -phosphinyl guanidine group, the nitrogen participating in a double bond with the central carbon atom of the guanidine core is referred to as the N 1 nitrogen atom, the nitrogen atom participating in a single bond with the central carbon atom of the guanidine core and a bond with the phosphorus atom of the phosphinyl group is referred to as the N 2 nitrogen atom, and the remaining nitrogen atom participating in a single bond with the central carbon atom of the guanidine core is referred to as the N 3 nitrogen atom.
- a guanidine core or an N 2 -phosphinyl guanidine group can be a portion of a larger group (or compound) which does not contain guanidine in its name.
- the compound 7-dimethylphosphinylimidazo[1,2-a]imidazole could be classified as a compound having an imidazo[1,2-a]imidazole core (or a compound having a phosphinylimidazo[1,2-a]imidazole group)
- 7-dimethylphosphinylimidazo[1,2-a]imidazole would still be classified as a compound having a guanidine core (or as a compound having an N 2 -phosphinyl guanidine group) since it contains the defined general structure of the guanidine core (or the N 2 -phosphinyl guanidine group).
- an N 2 -phosphinyl guanidine compound can have Structure Gu1, Structure Gu2, Structure Gu3, Structure Gu4, or Structure Gu5; alternatively, Structure Gu1; alternatively, Structure Gu2; alternatively, Structure Gu3; alternatively, Structure Gu4; or alternatively, Structure Gu5.
- an N 2 -phosphinyl guanidine chromium complex (e.g., a chromium containing compound complexed to an N 2 -phosphinyl guanidine compound) can have Structure GuCr1, Structure GuCr2, Structure GuCr3, Structure GuCr4, or Structure GuCr5; alternatively, Structure GuCr1; alternatively, Structure GuCr2; alternatively, Structure GuCr3; alternatively, Structure GuCr4; or alternatively, Structure GuCr5.
- N 2 -phosphinyl guanidine compound Structures Gu1, Gu2, Gu3, Gu4, and/or Gu5, and/or ii) N 2 -phosphinyl guanidine chromium complex Structures GuCr1, GuCr2, GuCr3, GuCr4 and/or GuCr5 are independently described herein and can be utilized without limitation to further describe the appropriate i) N 2 -phosphinyl guanidine compound Structures Gu1, Gu2, Gu3, Gu4, and/or Gu5, and/or ii) N 2 -phosphinyl guanidine chromium complex Structures GuCr1, GuCr2, GuCr3, GuCr4, and/or GuCr5.
- CrX p within the N 2 -phosphinyl guanidine chromium complex Structures GuCr1, GuCr2, GuCr3, GuCr4, and/or GuCr5 represents the chromium containing compound of the N 2 -phosphinyl guanidine chromium complexes.
- Q represents an optional neutral ligand of the N 2 -phosphinyl guanidine chromium complex Structures GuCr1, GuCr2, GuCr3, GuCr4, and/or GuCr5, while q represents the number of optional neutral ligands present.
- CrX p , Q, and q are independently described herein and can be utilized without limitation to further describe the N 2 -phosphinyl guanidine chromium complex Structures GuCr1, GuCr2, GuCr3, GuCr4, and/or GuCr5. Additionally, CrX p , Q, and q can be combined with the independently described R 1 , R 2a , R 2b , R 3 , R 4 , and R 5 to further describe the N 2 -phosphinyl guanidine chromium complex Structures GuCr1, GuCr2, GuCr3, GuCr4, and/or GuCr5.
- R 1 for the N 2 -phosphinyl formamidine compounds, the N 2 -phosphinyl formamidine chromium complexes, the N 2 -phosphinyl amidine compounds, the N 2 -phosphinyl amidine chromium complexes, the N 2 -phosphinyl guanidine compounds, and/or the N 2 -phosphinyl guanidine chromium complexes, which have an R 1 group can be an organyl group; alternatively, an organyl group consisting essentially of inert functional groups; or alternatively, a hydrocarbyl group.
- the R 1 organyl group for the N 2 -phosphinyl formamidine compounds, the N 2 -phosphinyl formamidine chromium complexes, the N 2 -phosphinyl amidine compounds, the N 2 -phosphinyl amidine chromium complexes, the N 2 -phosphinyl guanidine compounds, and/or the N 2 -phosphinyl guanidine chromium complexes, which have an R 1 group can be a C 1 to C 30 organyl group; alternatively, a C 1 to C 20 organyl group; alternatively, a C 1 to C 15 organyl group; alternatively, a C 1 to C 10 organyl group; or alternatively, a C 1 to C 5 organyl group.
- the R 1 organyl group consisting essentially of inert functional groups for the N 2 -phosphinyl formamidine compounds, the N 2 -phosphinyl formamidine chromium complexes, the N 2 -phosphinyl amidine compounds, the N 2 -phosphinyl amidine chromium complexes, the N 2 -phosphinyl guanidine compounds, and/or the N 2 -phosphinyl guanidine chromium complexes, which have an R 1 group can be a C 1 to C 30 organyl group consisting essentially of inert functional groups; alternatively, a C 1 to C 20 organyl group consisting essentially of inert functional groups; alternatively, a C 1 to C 15 organyl group consisting essentially of inert functional groups; alternatively, a C 1 to C 10 organyl group consisting essentially of inert functional groups; or alternatively, a C 1 to C 5 organyl group consist
- the R 1 hydrocarbyl group for the N 2 -phosphinyl formamidine compounds, the N 2 -phosphinyl formamidine chromium complexes, the N 2 -phosphinyl amidine compounds, the N 2 -phosphinyl amidine chromium complexes, the N 2 -phosphinyl guanidine compounds, and/or the N 2 -phosphinyl guanidine chromium complexes, which have an R 1 group can be a C 1 to C 30 hydrocarbyl group; alternatively, a C 1 to C 20 hydrocarbyl group; alternatively, a C 1 to C 15 hydrocarbyl group; alternatively, a C 1 to C 10 hydrocarbyl group; alternatively, a C 1 to C 5 hydrocarbyl group; alternatively, a C 1 to C 30 alkyl group; alternatively, a C 1 to C 20 alkyl group; alternatively, a C 1 to C 15 alkyl group
- the R 1 group for the N 2 -phosphinyl formamidine compounds, the N 2 -phosphinyl formamidine chromium complexes, the N 2 -phosphinyl amidine compounds, the N 2 -phosphinyl amidine chromium complexes, the N 2 -phosphinyl guanidine compounds, and/or the N 2 -phosphinyl guanidine chromium complexes, which have an R 1 group can be a C 3 to C 30 aromatic group; alternatively, a C 3 to C 20 aromatic group; alternatively, a C 3 to C 15 aromatic group; or alternatively, a C 3 to C 10 aromatic group.
- the R 1 group for the N 2 -phosphinyl formamidine compounds, the N 2 -phosphinyl formamidine chromium complexes, the N 2 -phosphinyl amidine compounds, the N 2 -phosphinyl amidine chromium complexes, the N 2 -phosphinyl guanidine compounds, and/or the N 2 -phosphinyl guanidine chromium complexes, which have an R 1 group can be a phenyl group or a C 6 to C 30 substituted phenyl group; alternatively, a phenyl group or a C 6 to C 20 substituted phenyl group; alternatively, a phenyl group or a C 6 to C 15 substituted phenyl group; or alternatively, a phenyl group or a C 6 to C 10 substituted phenyl group.
- General substituent groups are provided herein (and will be described in more detail later herein) and these general substituent groups can be utilized to further describe the substituted phenyl groups which can be utilized as R 1 for the N 2 -phosphinyl formamidine compounds, the N 2 -phosphinyl formamidine chromium complexes, the N 2 -phosphinyl amidine compounds, the N 2 -phosphinyl amidine chromium complexes, the N 2 -phosphinyl guanidine compounds, and/or the N 2 -phosphinyl guanidine chromium complexes.
- R 2 for the N 2 -phosphinyl amidine compounds and/or the N 2 -phosphinyl amidine chromium complexes can be an organyl group; alternatively, an organyl group consisting essentially of inert functional groups; or alternatively, a hydrocarbyl group.
- R 2 for the N 2 -phosphinyl amidine compounds and/or the N 2 -phosphinyl amidine chromium complexes can be a C 1 to C 30 organyl group; alternatively, a C 1 to C 20 organyl group; alternatively, a C 1 to C 15 organyl group; alternatively, a C 1 to C 10 organyl group; or alternatively, a C 1 to C 5 organyl group.
- R 2 for the N 2 -phosphinyl amidine compounds and/or the N 2 -phosphinyl amidine chromium complexes can be a C 1 to C 30 organyl group consisting essentially of inert functional groups; alternatively, a C 1 to C 20 organyl group consisting essentially of inert functional groups; alternatively, a C 1 to C 15 organyl group consisting essentially of inert functional groups; alternatively, a C 1 to C 10 organyl group consisting essentially of inert functional groups; or alternatively, a C 1 to C 5 organyl group consisting essentially of inert functional groups.
- R 2 for the N 2 -phosphinyl amidine compounds and/or the N 2 -phosphinyl amidine chromium complexes can be a C 1 to C 30 hydrocarbyl group; alternatively, a C 1 to C 20 hydrocarbyl group; alternatively, a C 1 to C 15 hydrocarbyl group; alternatively, a C 1 to C 10 hydrocarbyl group; alternatively, a C 1 to C 5 hydrocarbyl group; alternatively, a C 1 to C 30 alkyl group; alternatively, a C 1 to C 20 alkyl group; alternatively, a C 1 to C 15 alkyl group; alternatively, a C 1 to C 10 alkyl group; or alternatively, a C 1 to C 5 alkyl group.
- R 2 for the N 2 -phosphinyl amidine compounds and/or the N 2 -phosphinyl amidine chromium complexes can be a C 3 to C 30 aromatic group; alternatively, a C 3 to C 20 aromatic group; alternatively, a C 3 to C 15 aromatic group; or alternatively, a C 3 to C 10 aromatic group.
- R 2 for the N 2 -phosphinyl amidine compounds and/or the N 2 -phosphinyl amidine chromium complexes can be a phenyl group or a C 6 to C 30 substituted phenyl group; alternatively, a phenyl group or a C 6 to C 20 substituted phenyl group; alternatively, a phenyl group or a C 6 to C 15 substituted phenyl group; or alternatively, a phenyl group or a C 6 to C 10 substituted phenyl group.
- R 2 for the N 2 -phosphinyl amidine compounds and/or the N 2 -phosphinyl amidine chromium complexes can be a benzyl group or a C 6 to C 30 substituted benzyl group; alternatively, a benzyl group or a C 6 to C 20 substituted benzyl group; alternatively, a benzyl group or a C 6 to C 15 substituted benzyl group; or alternatively, a benzyl group or a C 6 to C 10 substituted benzyl group.
- General substituent groups are provided herein and these general substituent groups can be utilized to further describe the substituted phenyl groups and/or substituted benzyl groups which can be utilized as R 2 for the N 2 -phosphinyl amidine compounds and/or the N 2 -phosphinyl amidine chromium complexes.
- R 2a and/or R 2b for the N 2 -phosphinyl guanidine compounds and/or the N 2 -phosphinyl guanidine chromium complexes which have an R 2a and/or R 2b group independently can be hydrogen or an organyl group; alternatively, hydrogen; or alternatively, an organyl group.
- R 2a and/or R 2b for the N 2 -phosphinyl guanidine compounds and/or the N 2 -phosphinyl guanidine chromium complexes which have an R 2a and/or R 2b group independently can be hydrogen or an organyl group consisting essentially of inert functional groups; alternatively, hydrogen; or alternatively, an organyl group consisting essentially of inert functional groups.
- R 2a and/or R 2b for the N 2 -phosphinyl guanidine compounds and/or the N 2 -phosphinyl guanidine chromium complexes which have an R 2a and/or R 2b group independently can be hydrogen or a hydrocarbyl group; alternatively, hydrogen; or alternatively, a hydrocarbyl group.
- R 2a and/or R 2b organyl group for the N 2 -phosphinyl guanidine compounds and/or the N 2 -phosphinyl guanidine chromium complexes which have an R 2a and/or R 2b organyl group independently can be a C 1 to C 30 organyl group; alternatively, a C 1 to C 20 organyl group; alternatively, a C 1 to C 15 organyl group; alternatively, a C 1 to C 10 organyl group; or alternatively, a C 1 to C 5 organyl group.
- R 2a and/or R 2b organyl group consisting essentially of inert functional group for the N 2 -phosphinyl guanidine compounds and/or the N 2 -phosphinyl guanidine chromium complexes which have an R 2a and/or R 2b organyl group consisting essentially of inert functional groups independently can be a C 1 to C 30 organyl group consisting essentially of inert functional groups; alternatively, a C 1 to C 20 organyl group consisting essentially of inert functional groups; alternatively, a C 1 to C 15 organyl group consisting essentially of inert functional groups; alternatively, a C 1 to C 10 organyl group consisting essentially of inert functional groups; or alternatively, a C 1 to C 5 organyl group consisting essentially of inert functional groups.
- R 2a and/or R 2b hydrocarbyl group for the N 2 -phosphinyl guanidine compounds and/or the N 2 -phosphinyl guanidine chromium complexes which have an R 2a and/or R 2b hydrocarbyl group independently can be a C 1 to C 30 hydrocarbyl group; alternatively, a C 1 to C 20 hydrocarbyl group; alternatively, a C 1 to C 15 hydrocarbyl group; alternatively, a C 1 to C 10 hydrocarbyl group; alternatively, a C 1 to C 5 hydrocarbyl group; alternatively, a C 1 to C 30 alkyl group; alternatively, a C 1 to C 20 alkyl group; alternatively, a C 1 to C 15 alkyl group; alternatively, a C 1 to C 10 alkyl group; or alternatively, a C 1 to C 5 alkyl group.
- R 2a and/or R 2b group for the N 2 -phosphinyl guanidine compounds and/or the N 2 -phosphinyl guanidine chromium complexes which have an R 2a and/or R 2b group independently can be a C 3 to C 30 aromatic group; alternatively, a C 3 to C 20 aromatic group; alternatively, a C 3 to C 15 aromatic group; or alternatively, a C 3 to C 10 aromatic group.
- R 2a and/or R 2b group for the N 2 -phosphinyl guanidine compounds and/or the N 2 -phosphinyl guanidine chromium complexes which have an R 2a and/or R 2b group independently can be a phenyl group or a C 6 to C 30 substituted phenyl group; alternatively, a phenyl group or a C 6 to C 20 substituted phenyl group; alternatively, a phenyl group or a C 6 to C 15 substituted phenyl group; or alternatively, a phenyl group or a C 6 to C 10 substituted phenyl group.
- General substituent groups are provided herein and these general substituent groups can be utilized to further describe the substituted phenyl groups which can be utilized as R 2a and/or R 2b for the N 2 -phosphinyl guanidine compounds and/or the N 2 -phosphinyl guanidine chromium complexes.
- R 1 and R 2a of the N 2 -phosphinyl guanidine compounds and/or the N 2 -phosphinyl guanidine chromium complexes can be joined to form a group, L 12 (e.g., linking group L 12 ), wherein L 12 , the N 1 nitrogen atom, and the N 3 nitrogen atom can form a ring or a ring system.
- L 12 e.g., linking group L 12
- R 3 and R 2b of the N 2 -phosphinyl guanidine compounds and/or the N 2 -phosphinyl guanidine chromium complexes can be joined to form a group, L 23 (e.g., linking group L 23 ), wherein L 23 , the N 2 nitrogen atom, and the N 3 nitrogen atom can form a ring or a ring system.
- L 23 e.g., linking group L 23
- L 12 and/or L 23 group for the N 2 -phosphinyl guanidine compounds and/or the N 2 -phosphinyl guanidine chromium complexes which have an L 12 and/or L 23 group independently can be an organylene group; alternatively, an organylene group consisting of inert functional groups; or alternatively, a hydrocarbylene group.
- the organylene group which can be utilized as an L 12 and/or L 23 group of the N 2 -phosphinyl guanidine compounds and/or the N 2 -phosphinyl guanidine chromium complexes, which have an L 12 and/or L 23 group independently can be a C 2 to C 20 organylene group; alternatively, a C 2 to C 15 organylene group; alternatively, a C 2 to C 10 organylene group; or alternatively, a C 2 to C 5 organylene group.
- the organylene group consisting of inert functional groups which can be utilized as an L 12 and/or L 23 group of the N 2 -phosphinyl guanidine compounds and/or the N 2 -phosphinyl guanidine chromium complexes, which have an L 12 and/or L 23 group can be a C 2 to C 20 organylene group consisting of inert functional groups; alternatively, a C 2 to C 15 organylene group consisting of inert functional groups; alternatively, a C 2 to C 10 organylene group consisting of inert functional groups; or alternatively, a C 2 to C 5 organylene group consisting of inert functional groups.
- the hydrocarbylene group which can be utilized as an L 12 and/or L 23 group of the N 2 -phosphinyl guanidine compounds and/or the N 2 -phosphinyl guanidine chromium complexes, which have an L 12 and/or L 23 group can be a C 2 to C 20 hydrocarbylene group; alternatively, a C 2 to C 15 hydrocarbylene group; alternatively, a C 2 to C 10 hydrocarbylene group; or alternatively, a C 2 to C 5 hydrocarbylene group.
- L 12 and/or L 23 can have any structure provided in Table 1.
- L 12 and/or L 23 can have Structure 1L, Structure 2L, Structure 3L, Structure 4L, or Structure 5L.
- L 12 and/or L 23 can have Structure 2L or Structure 3L; or alternatively, Structure 4L or Structure 5L.
- L 12 and/or L 23 can have Structure 1L; alternatively, Structure 2L; alternatively, Structure 3L; alternatively, Structure 4L; or alternatively, Structure 5L.
- L 12 or L 23 can have Structure 6L.
- the undesignated valencies represent points at which L 12 and/or L 23 , when present, attach to the respective nitrogen atoms of the N 2 -phosphinyl guanidine compound and/or N 2 -phosphinyl guanidine chromium complex.
- m can be an integer ranging from 2 to 5.
- m can be 2 or 3; alternatively, m can be 2; or alternatively, m can be 3.
- L 12 can have a structure that can comprise at least one substituent located on the carbon atom attached to the N 1 nitrogen atom of the N 2 -phosphinyl guanidine compound and/or the N 2 -phosphinyl guanidine chromium complex; alternatively, can comprise only one substituent located on the carbon atom attached to the N 1 nitrogen atom of the N 2 -phosphinyl guanidine compound and/or N 2 -phosphinyl guanidine chromium complex; or alternatively, can comprise two substituents located on the carbon atom attached to the N 1 nitrogen atom of the N 2 -phosphinyl guanidine compound and/or the N 2 -phosphinyl guanidine chromium complex.
- L 12 can have a structure that can consist of one substituent located on the carbon atom attached to the N 1 nitrogen atom of the N 2 -phosphinyl guanidine compound and/or the N 2 -phosphinyl guanidine chromium complex; or alternatively, can consist of two substituents located on the carbon atom attached to the N 1 nitrogen atom of the N 2 -phosphinyl guanidine compound and/or N 2 -phosphinyl guanidine chromium complex.
- R 2a and R 2b of the N 2 -phosphinyl guanidine compounds and/or the N 2 -phosphinyl guanidine chromium complexes can be joined to form a group, L 22 (e.g., linking group L 22 ), wherein R 2a , R 2b , and the N 3 nitrogen (or L 22 and the N 3 nitrogen) can form a ring or ring system.
- L 22 e.g., linking group L 22
- L 22 of the N 2 -phosphinyl guanidine compounds and/or the N 2 -phosphinyl guanidine chromium complexes, which have an L 22 group can be an organylene group; alternatively, an organylene group consisting of inert functional groups; or alternatively, a hydrocarbylene group.
- the organylene group which can be utilized as L 22 of the N 2 -phosphinyl guanidine compounds and/or the N 2 -phosphinyl guanidine chromium complexes having an L 22 group can be a C 3 to C 20 organylene group; alternatively, a C 3 to C 15 organylene group; or alternatively, a C 3 to C 10 organylene group.
- the organylene group consisting of inert functional groups which can be utilized as L 22 of the N 2 -phosphinyl guanidine compounds and/or the N 2 -phosphinyl guanidine chromium complexes having an L 22 group can be a C 3 to C 20 organylene group consisting of inert functional groups; alternatively, a C 3 to C 15 organylene group consisting of inert functional groups; or alternatively, a C 3 to C 10 organylene group consisting of inert functional groups.
- the hydrocarbylene group which can be utilized as L 22 of the N 2 -phosphinyl guanidine compounds and/or the N 2 -phosphinyl guanidine chromium complexes having an L 22 group can be a C 4 to C 20 hydrocarbylene group; alternatively, a C 4 to C 15 hydrocarbylene group; or alternatively, a C 4 to C 10 hydrocarbylene group.
- L 22 can have any structure provided in Table 2. In some embodiments, L 22 can have Structure 11L, Structure 12L, Structure 13L, Structure 14L, or Structure 15L. In other embodiments, L 22 can have Structure 11L; alternatively, Structure 12L; alternatively, Structure 13L; alternatively, Structure 14L; or alternatively, Structure 15L.
- n can be an integer ranging from 4 to 7. In further embodiments, n can be 4 or 5; alternatively, n can be 4; or alternatively, n can be 5.
- L 22 can be a but-1,4-ylene group, a pent-1,4-ylene group, a pent-1,5-ylene group, a hex-2,5-ylene group, a hex-1,5-ylene group, a hept-2,5-ylene group, a buta-1,3-dien-1,4-ylene group, or a bis(eth-2-yl)ether group; alternatively, a but-1,4-ylene group, a pent-1,5-ylene group, or a bis(eth-2-yl)ether group; alternatively, a but-1,4-ylene group; alternatively, a pent-1,5-ylene group; alternatively, a buta-1,3-dien-1,4-ylene group; or
- R 3 of the N 2 -phosphinyl formamidine compounds, the N 2 -phosphinyl formamidine chromium complexes, the N 2 -phosphinyl amidine compounds, the N 2 -phosphinyl amidine chromium complexes, the N 2 -phosphinyl guanidine compounds, and/or the N 2 -phosphinyl guanidine chromium complexes, which have an R 3 group can be hydrogen or an organyl group; hydrogen or an organyl group consisting essentially of inert functional groups; alternatively, hydrogen or a hydrocarbyl group; alternatively, hydrogen; alternatively, an organyl group; alternatively, an organyl group consisting essentially of inert functional groups; or alternatively, a hydrocarbyl group.
- the organyl group which can be utilized as R 3 of the N 2 -phosphinyl formamidine compounds, the N 2 -phosphinyl formamidine chromium complexes, the N 2 -phosphinyl amidine compounds, the N 2 -phosphinyl amidine chromium complexes, the N 2 -phosphinyl guanidine compounds, and/or the N 2 -phosphinyl guanidine chromium complexes, which have an R 3 group can be a C 1 to C 30 organyl group; alternatively, a C 1 to C 20 organyl group; alternatively, a C 1 to C 15 organyl group; alternatively, a C 1 to C 10 organyl group; or alternatively, a C 1 to C 5 organyl group.
- the organyl group consisting of inert functional groups which can be utilized as R 3 of the N 2 -phosphinyl formamidine compounds, the N 2 -phosphinyl formamidine chromium complexes, the N 2 -phosphinyl amidine compounds, the N 2 -phosphinyl amidine chromium complexes, the N 2 -phosphinyl guanidine compounds, and/or the N 2 -phosphinyl guanidine chromium complexes, which have an R 3 group can be a C 1 to C 30 organyl group consisting essentially of inert functional groups; alternatively, a C 1 to C 20 organyl group consisting essentially of inert functional groups; alternatively, a C 1 to C 15 organyl group consisting essentially of inert functional groups; alternatively, a C 1 to C 10 organyl group consisting essentially of inert functional groups; or alternatively, a C 1 to C 5 organyl group consisting
- the hydrocarbyl group which can be utilized as R 3 of the N 2 -phosphinyl formamidine compounds, the N 2 -phosphinyl formamidine chromium complexes, the N 2 -phosphinyl amidine compounds, the N 2 -phosphinyl amidine chromium complexes, the N 2 -phosphinyl guanidine compounds, and/or the N 2 -phosphinyl guanidine chromium complexes, which have an R 3 group can be a C 1 to C 30 hydrocarbyl group; alternatively, a C 1 to C 20 hydrocarbyl group; alternatively, a C 1 to C 15 hydrocarbyl group; alternatively, a C 1 to C 10 hydrocarbyl group; or alternatively, a C 1 to C 5 hydrocarbyl group.
- R 3 of the N 2 -phosphinyl formamidine compounds, the N 2 -phosphinyl formamidine chromium complexes, the N 2 -phosphinyl amidine compounds, the N 2 -phosphinyl amidine chromium complexes, the N 2 -phosphinyl guanidine compounds, and/or the N 2 -phosphinyl guanidine chromium complexes, which have an R 3 group can be a C 1 to C 30 alkyl group; alternatively, a C 1 to C 20 alkyl group; alternatively, a C 1 to C 15 alkyl group; alternatively, a C 1 to C 10 alkyl group; or alternatively, a C 1 to C 5 alkyl group.
- R 3 of the N 2 -phosphinyl formamidine compounds, the N 2 -phosphinyl formamidine chromium complexes, the N 2 -phosphinyl amidine compounds, the N 2 -phosphinyl amidine chromium complexes, the N 2 -phosphinyl guanidine compounds, and/or the N 2 -phosphinyl guanidine chromium complexes, which have an R 3 group can be a C 3 to C 30 aromatic group; alternatively, a C 3 to C 20 aromatic group; alternatively, a C 3 to C 15 aromatic group; or alternatively, a C 3 to C 10 aromatic group.
- R 3 of the N 2 -phosphinyl formamidine compounds, the N 2 -phosphinyl formamidine chromium complexes, the N 2 -phosphinyl amidine compounds, the N 2 -phosphinyl amidine chromium complexes, the N 2 -phosphinyl guanidine compounds, and/or the N 2 -phosphinyl guanidine chromium complexes, which have an R 3 group can be a phenyl group or a C 6 to C 30 substituted phenyl group; alternatively, a phenyl group or a C 6 to C 20 substituted phenyl group; alternatively, a phenyl group or a C 6 to C 15 substituted phenyl group; or alternatively, a phenyl group or a C 6 to C 10 substituted phenyl group.
- General substituent groups are provided herein and these general substituent groups can be utilized to further describe the substituted phenyl groups which can be utilized as R 3 for the N 2 -phosphinyl formamidine compounds, the N 2 -phosphinyl formamidine chromium complexes, the N 2 -phosphinyl amidine compounds, the N 2 -phosphinyl amidine chromium complexes, the N 2 -phosphinyl guanidine compounds, and/or the N 2 -phosphinyl guanidine chromium complexes.
- R 4 and R 5 of the N 2 -phosphinyl formamidine compounds, the N 2 -phosphinyl formamidine chromium complexes, the N 2 -phosphinyl amidine compounds, the N 2 -phosphinyl amidine chromium complexes, the N 2 -phosphinyl guanidine compounds, and/or the N 2 -phosphinyl guanidine chromium complexes can be joined to form a ring (regardless of particular type of group - organyl, organyl consisting of inert functional groups, hydrocarbyl, or any species within) containing the phosphorus atom of the N 2 -phosphinyl formamidine compound, the N 2 -phosphinyl formamidine chromium complex, the N 2 -phosphinyl amidine compound, the N 2 -phosphinyl amidine chromium complex, the N 2 -phosphinyl guan
- General substituent groups are provided herein and these general substituent groups can be utilized to further describe the substituted phenyl groups which can be utilized as R 4 and/or R 5 for the N 2 -phosphinyl formamidine compounds, the N 2 -phosphinyl formamidine chromium complexes, the N 2 -phosphinyl amidine compounds, the N 2 -phosphinyl amidine chromium complexes, the N 2 -phosphinyl guanidine compounds, and/or the N 2 -phosphinyl guanidine chromium complexes.
- Each substituent (alternatively, substituent group, or alternatively, general substituent group) or non-hydrogen substituent (or alternatively, non-hydrogen substituent group) can be a halide, a hydrocarbyl group, or a hydrocarboxy group; alternatively, a halide or a hydrocarbyl group; alternatively, a halide or a hydrocarboxy group; alternatively, a hydrocarbyl group or a hydrocarboxy group; alternatively, a halide; alternatively, a hydrocarbyl group; or alternatively, a hydrocarboxy group.
- each substituent or non-hydrogen substituent of any aspect or embodiment calling for a substituent independently can be a halide, a C 1 to C 10 hydrocarbyl group, or a C 1 to C 10 hydrocarboxy group; alternatively, a halide or a C 1 to C 10 hydrocarbyl group; alternatively, a halide or a C 1 to C 10 hydrocarboxy group; alternatively, a C 1 to C 10 hydrocarbyl group or a C 1 to C 10 hydrocarboxy group; alternatively, a halide; alternatively, a C 1 to C 10 hydrocarbyl group; or alternatively, a C 1 to C 10 hydrocarboxy group.
- each substituent or non-hydrogen substituent of any aspect or embodiment calling for a substituent independently can be a halide, a C 1 to C 5 hydrocarbyl group, or a C 1 to C 5 hydrocarboxy group; alternatively, a halide or a C 1 to C 5 hydrocarbyl group; alternatively, a halide or a C 1 to C 5 hydrocarboxy group; alternatively, a C 1 to C 5 hydrocarbyl group or a C 1 to C 5 hydrocarboxy group; alternatively, a halide; alternatively, a C 1 to C 5 hydrocarbyl group; or alternatively, a C 1 to C 5 hydrocarboxy group.
- each halide substituent of any aspect or embodiment calling for a substituent or non-hydrogen substituent independently can be fluoride, chloride, bromide, or iodide; or alternatively, fluoride or chloride. In some embodiments, each halide substituent of any aspect or embodiment calling for a substituent or non-hydrogen substituent independently can be fluoride; alternatively, chloride; alternatively, bromide; or alternatively, iodide.
- each hydrocarbyl substituent of any aspect or embodiment calling for a substituent or non-hydrogen substituent independently can be an alkyl group, an aryl group, or an aralkyl group; alternatively, an alkyl group; alternatively, an aryl group; or alternatively, an aralkyl group.
- each alkyl substituent of any aspect or embodiment calling for a substituent or non- hydrogen substituent independently can be a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a 2-pentyl group, a 3-pentyl group, a 2-methyl-1-butyl group, a tert-pentyl group, a 3-methyl-1-butyl group, a 3-methyl-2-butyl group, or a neo-pentyl group; alternatively, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, or a neo-pentyl group; alternatively, a methyl group; alternatively, an ethyl group, an iso
- each aryl substituent of any aspect or embodiment calling for a substituent or non-hydrogen substituent independently can be a phenyl group, a tolyl group, a xylyl group, or a 2,4,6-trimethylphenyl group; alternatively, a phenyl group; alternatively, a tolyl group; alternatively, a xylyl group; or alternatively, a 2,4,6-trimethylphenyl group.
- each aralkyl substituent of any aspect or embodiment calling for a substituent or non-hydrogen substituent independently can be a benzyl group or an ethylphenyl group (2-phenyleth-1-yl or 1-phenyleth-1-yl); alternatively, a benzyl group; alternatively, an ethylphenyl group; alternatively a 2-phenyleth-1-yl group; or alternatively, a 1-phenyleth-1-yl group.
- each hydrocarboxy substituent of any aspect or embodiment calling for a substituent or non-hydrogen substituent independently can be an alkoxy group, an aryloxy group, or an aralkoxy group; alternatively, an alkoxy group; alternatively, an aryloxy group; or alternatively, an aralkoxy group.
- each alkoxy substituent of any aspect or embodiment calling for a substituent or non-hydrogen substituent independently can be a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxy group, an isobutoxy group, a tert-butoxy group, an n-pentoxy group, a 2-pentoxy group, a 3-pentoxy group, a 2-methyl-1-butoxy group, a tert-pentoxy group, a 3-methyl-1-butoxy group, a 3-methyl-2-butoxy group, or a neo-pentoxy group; alternatively, a methoxy group, an ethoxy group, an isopropoxy group, a tert-butoxy group, or a neo-pentoxy group; alternatively, a methoxy group; alternatively, an ethoxy group; alternatively, an isopropoxy group; alternatively, a tert-
- each aryloxy substituent of any aspect or embodiment calling for a substituent or non-hydrogen substituent independently can be a phenoxy group, a toloxy group, a xyloxy group, or a 2,4,6-trimethylphenoxy group; alternatively, a phenoxy group; alternatively, a toloxy group; alternatively, a xyloxy group; or alternatively, a 2,4,6-trimethylphenoxy group.
- each aralkoxy substituent of any aspect or embodiment calling for a substituent or non-hydrogen substituent independently can be a benzoxy group.
- the neutral ligand, Q, of the N 2 -phosphinyl formamidine chromium complexes, the N 2 -phosphinyl amidine chromium complexes, and/or the N 2 -phosphinyl guanidine chromium complexes independently can be any neutral ligand that forms an isolatable compound with the N 2 -phosphinyl formamidine chromium complexes, the N 2 -phosphinyl amidine chromium complexes, and/or the N 2 -phosphinyl guanidine chromium complexes.
- each neutral ligand independently can be a nitrile or an ether.
- the neutral ligand can be a nitrile; or alternatively, an ether.
- the number of neutral ligands, q, of the N 2 -phosphinyl formamidine chromium complexes, the N 2 -phosphinyl amidine chromium complexes, and/or the N 2 -phosphinyl guanidine chromium complexes can be any number that forms an isolatable compound with the N 2 -phosphinyl formamidine chromium complexes, the N 2 -phosphinyl amidine chromium complexes, and/or the N 2 -phosphinyl guanidine chromium complexes.
- the number of neutral ligands can be from 0 to 6; alternatively, from 0 to 3; alternatively, 0; alternatively, 1; alternatively, 2; alternatively, 3; or alternatively, 4.
- each neutral nitrile ligand independently can be a C 2 to C 20 nitrile; or alternatively, a C 2 to C 10 nitrile.
- each neutral nitrile ligand independently can be a C 2 to C 20 aliphatic nitrile, a C 7 to C 20 aromatic nitrile, a C 8 to C 20 aralkane nitrile, or combinations thereof; alternatively, a C 2 to C 20 aliphatic nitrile; alternatively, a C 7 to C 20 aromatic nitrile; or alternatively, a C 8 to C 20 aralkane nitrile.
- each neutral nitrile ligand independently can be a C 2 to C 10 aliphatic nitrile, a C 7 to C 10 aromatic nitrile, a C 8 to C 10 aralkane nitrile, or combinations thereof; alternatively, a C 1 to C 10 aliphatic nitrile; alternatively, a C 7 to C 10 aromatic nitrile; or alternatively, a C 8 to C 10 aralkane nitrile.
- each neutral nitrile ligand independently can be acetonitrile, propionitrile, a butyronitrile, benzonitrile, or combinations thereof; alternatively, acetonitrile; alternatively, propionitrile; alternatively, a butyronitrile; or alternatively, benzonitrile.
- each neutral ether ligand independently can be a C 2 to C 40 ether; alternatively, a C 2 to C 30 ether; or alternatively, a C 2 to C 20 ether.
- each neutral ether ligand independently can be a C 2 to C 40 aliphatic ether, a C 3 to C 40 aliphatic cyclic ether, or a C 4 to C 40 aromatic cyclic ether; alternatively, a C 2 to C 40 aliphatic acyclic ether, or a C 3 to C 40 aliphatic cyclic ether; alternatively, a C 2 to C 40 aliphatic acyclic ether; alternatively, a C 3 to C 40 aliphatic cyclic ether; or alternatively, a C 4 to C 40 aromatic cyclic ether.
- each neutral ether ligand independently can be a C 2 to C 30 aliphatic ether, a C 3 to C 30 aliphatic cyclic ether, or a C 4 to C 30 aromatic cyclic ether; alternatively, a C 2 to C 30 aliphatic acyclic ether, or a C 3 to C 30 aliphatic cyclic ether; alternatively, a C 2 to C 30 aliphatic acyclic ether; alternatively, a C 3 to C 30 aliphatic cyclic ether; or alternatively, a C 4 to C 30 aromatic cyclic ether.
- each neutral ether ligand independently can be a C 2 to C 20 aliphatic ether, a C 3 to C 20 aliphatic cyclic ether, or a C 4 to C 20 aromatic cyclic ether; alternatively, a C 2 to C 20 aliphatic acyclic ether, or a C 3 to C 20 aliphatic cyclic ether; alternatively, a C 2 to C 20 aliphatic acyclic ether; alternatively, a C 3 to C 20 aliphatic cyclic ether; or alternatively, a C 4 to C 20 aromatic cyclic ether.
- each neutral ether ligand independently can be dimethyl ether, diethyl ether, a dipropyl ether, a dibutyl ether, methyl ethyl ether, a methyl propyl ether, a methyl butyl ether, tetrahydrofuran, a dihydrofuran, 1,3-dioxolane, tetrahydropyran, a dihydropyran, a pyran, a dioxane, furan, benzofuran, isobenzofuran, dibenzofuran, diphenyl ether, a ditolyl ether, or combinations thereof; alternatively, dimethyl ether, diethyl ether, a dipropyl ether, a dibutyl ether, methyl ethyl ether, a methyl propyl ether, a methyl butyl ether, or combinations thereof; alternatively, tetrahydrofuran,
- the metal alkyl compound can be an alkylaluminum compound.
- the alkylaluminum compound can be a trialkylaluminum compound, an alkylaluminum halide, an alkylaluminum alkoxide, an aluminoxane, or combinations thereof.
- the alkylaluminum compound can be a trialkylaluminum compound, an alkylaluminum halide, an aluminoxane, or combinations thereof; alternatively, a trialkylaluminum compound, an alkylaluminum halide, or combinations thereof; or alternatively, a trialkylaluminum compound, an aluminoxane, or combinations thereof.
- the alkylaluminum compound can be a trialkylaluminum compound; alternatively, an alkylaluminum halide; alternatively, an alkylaluminum alkoxide; or alternatively, an aluminoxane.
- the aluminoxane can have a repeating unit characterized by Formula I: wherein R' can be a linear or branched alkyl group.
- R' can be a linear or branched alkyl group.
- Alkyl groups for metal alkyl compounds (or alternatively, alkylaluminum compounds) are independently described herein and can be utilized without limitation to further describe the aluminoxanes having Formula I.
- n of Formula I can be greater than 1; or alternatively, greater than 2. In an embodiment, n can range from 2 to 15; or alternatively, from 3 to 10.
- each halide of any alkylaluminum halide disclosed herein independently can be fluoride, chloride, bromide, or iodide; or alternatively, chloride, bromide, or iodide.
- each halide of any metal alkyl halide disclosed herein can be fluoride; alternatively, chloride; alternatively, bromide; or alternatively, iodide.
- each alkyl group of any alkylaluminum compound disclosed herein independently can be a C 1 to C 20 alkyl group; alternatively, a C 1 to C 10 alkyl group; or alternatively, a C 1 to C 6 alkyl group.
- each alkyl group of any alkylaluminum compound disclosed herein independently can be a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, or an octyl group; or alternatively, a methyl group, an ethyl group, a butyl group, a hexyl group, or an octyl group.
- each alkyl group of any alkylaluminum compound disclosed herein independently can be a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an iso-butyl group, an n-hexyl group, or an n-octyl group; alternatively, a methyl group, an ethyl group, an n-butyl group, or an iso-butyl group; alternatively, a methyl group; alternatively, an ethyl group; alternatively, an n-propyl group; alternatively, an n-butyl group; alternatively, an iso-butyl group; alternatively, an n-hexyl group; or alternatively, an n-octyl group.
- each alkoxide group of any alkylaluminum alkoxide disclosed herein independently can be a C 1 to C 20 alkoxy group; alternatively, a C 1 to C 10 alkoxy group; or alternatively, a C 1 to C 6 alkoxy group.
- each alkoxide group of any alkylaluminum alkoxide disclosed herein independently can be a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a hexoxy group, a heptoxy group, or an octoxy group; or alternatively, a methoxy group, an ethoxy group, a butoxy group, a hexoxy group, or an octoxy group.
- each alkoxide group of any alkylaluminum alkoxide disclosed herein independently can be a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, an iso-butoxy group, an n-hexoxy group, or an n-octoxy group; alternatively, a methoxy group, an ethoxy group, an n-butoxy group, or an iso-butoxy group; alternatively, a methoxy group; alternatively, an ethoxy group; alternatively, an n-propoxy group; alternatively, an n-butoxy group; alternatively, an iso-butoxy group; alternatively, an n-hexoxy group; or alternatively, an n-octoxy group.
- the trialkylaluminum compound can comprise, can consist essentially of, or can be, trimethylaluminum, triethylaluminum, tripropylaluminum, tributylaluminum, trihexylaluminum, trioctylaluminum, or combinations thereof.
- the trialkylaluminum compound can comprise, can consist essentially of, or can be trimethylaluminum, triethylaluminum, tripropylaluminum, tri-n-butylaluminum, tri-isobutylaluminum, trihexylaluminum, tri-n-octylaluminum, or combinations thereof; alternatively, triethylaluminum, tri-n-butylaluminum, tri-isobutylaluminum, trihexylaluminum, tri-n-octylaluminum, or combinations thereof; alternatively, triethylaluminum, tri-n-butylaluminum, trihexylaluminum, tri-n-octylaluminum, or combinations thereof.
- the trialkylaluminum compound can comprise, can consist essentially of, or can be, trimethylaluminum; alternatively, triethylaluminum; alternatively, tripropylaluminum; alternatively, tri-n-butylaluminum; alternatively, tri-isobutylaluminum; alternatively, trihexylaluminum; or alternatively, tri-n-octylaluminum.
- the alkylaluminum halide can comprise, can consist essentially of, or can be, diethylaluminum chloride, diethylaluminum bromide, ethylaluminum dichloride, ethylaluminum sesquichloride, or combinations thereof.
- the alkylaluminum halide can comprise, can consist essentially of, or can be, diethylaluminum chloride, ethylaluminum dichloride, ethylaluminum sesquichloride, or combinations thereof.
- the alkylaluminum halide can comprise, can consist essentially of, or can be, diethylaluminum chloride; alternatively, diethylaluminum bromide; alternatively, ethylaluminum dichloride; or alternatively, ethylaluminum sesquichloride.
- the aluminoxane can comprise, can consist essentially of, or can be, methylaluminoxane (MAO), ethylaluminoxane, modified methylaluminoxane (MMAO), n-propylaluminoxane, iso-propyl-aluminoxane, n-butylaluminoxane, sec-butylaluminoxane, iso-butylaluminoxane, t-butylaluminoxane, 1-pentyl-aluminoxane, 2-entylaluminoxane, 3-pentyl-aluminoxane, iso-pentyl-aluminoxane, neopentylaluminoxane, or combinations thereof.
- MAO methylaluminoxane
- MMAO modified methylaluminoxane
- n-propylaluminoxane iso-propyl-aluminoxane
- the aluminoxane can comprise, can consist essentially of, or can be, methylaluminoxane (MAO), modified methylaluminoxane (MMAO), isobutyl aluminoxane, t-butyl aluminoxane, or combinations thereof.
- MAO methylaluminoxane
- MMAO modified methylaluminoxane
- isobutyl aluminoxane t-butyl aluminoxane, or combinations thereof.
- the aluminoxane can comprise, can consist essentially of, or can be, methylaluminoxane (MAO); alternatively, ethylaluminoxane; alternatively, modified methylaluminoxane (MMAO); alternatively, n-propylaluminoxane; alternatively, iso-propyl-aluminoxane; alternatively, n-butylaluminoxane; alternatively, sec-butylaluminoxane; alternatively, iso-butylaluminoxane; alternatively, t-butyl aluminoxane; alternatively, 1-pentyl-aluminoxane; alternatively, 2-pentylaluminoxane; alternatively, 3-pentyl-aluminoxane; alternatively, iso-pentyl-aluminoxane; or alternatively, neopentylaluminoxane.
- MAO methylaluminoxane
- MMAO
- the halogen containing compound can comprise a chloride containing compound, a bromide containing compound, an iodide containing compound, or combinations thereof.
- the halogen containing compound regardless of whether it is a chloride, bromide, or iodide containing compound, can comprise a metal halide, an alkyl metal halide, or an organic halide; alternatively, a metal halide; alternatively, an alkyl metal halide; or alternatively, an organic halide.
- the halogen containing compound can comprise a group 3 metal halide, a group 4 metal halide, a group 5 metal halide, a group 13 metal halide, a group 14 metal halide, a group 15 metal halide, or combinations thereof.
- Non-limiting examples of halogen containing compounds suitable for use in the present disclosure as an optional component of the catalyst system include scandium chloride, yttrium chloride, lanthanum chloride, titanium tetrachloride, zirconium tetrachloride, hafnium tetrachloride, boron trichloride, aluminum chloride, gallium chloride, silicon tetrachloride, trimethyl chlorosilane, germanium tetrachloride, tin tetrachloride, phosphorus trichloride, antimony trichloride, antimony pentachloride, bismuth trichloride, boron tribromide, aluminum tribromide, silicon tetrachloride, silicon tetrabromide, aluminum fluoride, molybdenum pentachloride, tungsten hexachloride, trityl hexachloroantimonate, or combinations thereof.
- the halogen containing compound can comprise a dialkylaluminum halide, an alkylaluminum dihalide, an alkylaluminum sesquihalide, or combinations thereof.
- the halogen containing compound can comprise diethylaluminum chloride, ethylaluminum sesquichloride, ethylaluminum dichloride, tributyltin chloride, dibutyltin dichloride, or combinations thereof; or alternatively, diethylaluminum chloride, ethylaluminum sesquichloride, ethylaluminum dichloride, or combinations thereof.
- the halogen containing compound can comprise a C 1 to C 15 organic halide; alternatively, a C 1 to C 10 organic halide; or alternatively, a C 1 to C 8 organic halide.
- halogen containing compounds suitable for use in the present disclosure as an optional component of the catalyst system include carbon tetrachloride, carbon tetrabromide, chloroform, bromoform, dichloromethane, dibromoethane, diiodomethane, chloromethane, bromomethane, iodomethane, dichloroethane, tetrachloroethane, trichloroacetone, hexachloroacetone, hexachlorocyclohexane, 1,3,5-trichlorobenzene, hexachlorobenzene, trityl chloride, benzyl chloride, benzyl bromide, benzyl iodide
- the catalyst system which can be utilized to produce the compositions disclosed herein can be selected from a catalyst system comprising a) a chromium containing compound, a pyrrole compound, a metal alkyl compound, and optionally a halide containing compound, b) a chromium containing compound, a diphosphino aminyl compound, and a metal alkyl compound, c) a chromium containing compound complexed to a diphosphino aminyl compound, and a metal alkyl compound, d) a chromium containing compound, an N 2 -phosphinyl amidine compound, and a metal alkyl compound, e) a chromium containing compound complexed to an N 2 -phosphinyl amidine compound, and a metal alkyl compound, f) a chromium containing compound, an N 2 -phosphinyl formamidine compound, and a metal alkyl compound, g
- the catalyst system which can be utilized to produce the compositions disclosed herein can be selected from the group consisting of a) a chromium containing compound, a pyrrole compound, an alkylaluminum compound, and optionally a halide containing compound, b) a chromium containing compound, a diphosphino aminyl compound, and an alkylaluminum compound, c) a chromium containing compound complexed to a diphosphino aminyl compound, and an alkylaluminum compound, d) a chromium containing compound, an N 2 -phosphinyl amidine compound, and an alkylaluminum compound, e) a chromium containing compound complexed to an N 2 -phosphinyl amidine compound, and an alkylaluminum compound, f) a chromium containing compound, an N 2 -phosphinyl formamidine compound, and an alkylalumin
- the catalyst system can comprise i) a chromium containing compound, ii) an amine, amide, or imide compound, iii) an alkylaluminum compound, and iv) optionally a halide containing compound.
- the catalyst system can comprise i) a chromium containing compound, ii) a pyrrole compound, iii) an alkylaluminum compound, and iv) optionally a halide containing compound.
- the catalyst systems using a pyrrole compound can be referred to as a "chromium-pyrrole catalyst systems.”
- the chromium-pyrrole catalyst system can be an ethylene trimerization catalyst system wherein the oligomer product (or trimerization product) typically comprises at least 70 wt.% hexenes.
- the chromium containing compound can comprise, or consist essentially of, a chromium carboxylate; and the alkylaluminum compound can comprise, or consist essentially of, a trialkylaluminum compound, a dialkylaluminum halide, an alkylaluminum dihalide, an alkylaluminum sesquihalide, or combinations thereof.
- the optional halide containing compound can be an organo halide compound, a metal halide compound (e.g., an inorganic metal halide compound or an alkyl metal halide compound), or combinations thereof.
- the catalyst system can comprise chromium(III) 2-ethylhexanoate, 2,5-dimethyl pyrrole, triethylaluminum, and diethylaluminum chloride. Additional information regarding the use of chromium-pyrrole catalyst systems for trimerizing ethylene (including specific examples) can be found in, but not limited to, EP 608447A1 ; EP 706983A1 ; U.S. Patent Nos.
- the catalyst system can comprise i) a chromium containing compound, ii) a diphosphino aminyl compound, and iii) an alkylaluminum compound; or alternatively, i) a chromium containing compound complexed to a diphosphino aminyl compound, and ii) an alkylaluminum compound.
- the catalyst systems using a diphosphino aminyl compound can be generically referred to as "chromium-PNP catalyst systems.”
- the chromium-PNP catalyst systems can be an ethylene tetramerization catalyst system wherein the oligomer product (or tetramerization product) comprises at least 70 wt. % octenes; or a trimerization and tetramerization catalyst system wherein the oligomer product (or trimerization and tetramerization product) comprises at least 70 wt. % hexenes and octenes.
- the chromium containing compound of the catalyst system or the chromium containing compound of the chromium containing compound complexed to a diphosphino aminyl compound of the catalyst system can comprise, or consist essentially of, a chromium halide, carboxylate, ⁇ -diketonate, hydrocarboxide, nitrate, sulfate, phosphate, or chlorate; alternatively, a chromium halide, carboxylate, or ⁇ -diketonate; alternatively, a chromium halide; alternatively, a chromium carboxylate; or alternatively, chromium ⁇ -diketonate.
- the alkylaluminum compound can comprise, or consist essentially of, a trialkylaluminum compound, an alkylaluminum halide (e.g., a dialkylaluminum halide, an alkylaluminum dihalide, and/or an alkylaluminum sesquihalide), an aluminoxane, or combinations thereof; or alternatively, an aluminoxane.
- an alkylaluminum halide e.g., a dialkylaluminum halide, an alkylaluminum dihalide, and/or an alkylaluminum sesquihalide
- aluminoxane e.g., a dialkylaluminum halide, an alkylaluminum dihalide, and/or an alkylaluminum sesquihalide
- aluminoxane e.g., a dialkylaluminum halide, an alkylaluminum dihalide, and/
- the catalyst system can comprise i) a chromium containing compound, ii) an N 2 -phosphinyl amidine compound, and iii) an alkylaluminum compound; or alternatively, i) a chromium containing compound complexed to an N 2 -phosphinyl amidine compound, and ii) an alkylaluminum compound.
- the catalyst systems using an N 2 -phosphinyl amidine compound can be generically referred to as "chromium-N 2 -phosphinyl amidine catalyst systems.”
- the chromium-N 2 -phosphinyl amidine catalyst systems can be an ethylene trimerization catalyst system wherein the oligomer product (or trimerization product) comprises at least 70 wt.% hexenes; or a trimerization and tetramerization catalyst system wherein the oligomer product (or trimerization and tetramerization product) comprises at least 70 wt.% hexenes and octenes.
- the chromium containing compound of the catalyst system or the chromium containing compound of the chromium containing compound complexed to an N 2 -phosphinyl amidine compound of the catalyst system can comprise, or consist essentially of, a chromium halide, carboxylate, ⁇ -diketonate, hydrocarboxide, nitrate, or chlorate; alternatively, a chromium halide, carboxylate, hydrocarboxide, or ⁇ -diketonate; alternatively, a chromium halide; alternatively, a chromium carboxylate; alternatively, a chromium hydrocarboxide; or alternatively, chromium ⁇ -diketonate.
- the alkylaluminum compound can comprise, or consist essentially of, a trialkylaluminum compound, an alkylaluminum halide (e.g., a dialkylaluminum halide, an alkylaluminum dihalide, and/or an alkylaluminum sesquihalide), an alkylaluminum alkoxide, an aluminoxane, or combinations thereof; or alternatively, an aluminoxane.
- an alkylaluminum halide e.g., a dialkylaluminum halide, an alkylaluminum dihalide, and/or an alkylaluminum sesquihalide
- an alkylaluminum alkoxide e.g., an aluminoxane, or combinations thereof; or alternatively, an aluminoxane.
- the catalyst system can comprise i) a chromium containing compound, ii) an N 2 -phosphinyl formamidine compound, and iii) an alkylaluminum compound; or alternatively, i) a chromium containing compound complexed to an N 2 -phosphinyl formamidine compound, and ii) an alkylaluminum compound.
- the catalyst systems using an N 2 -phosphinyl formamidine compound can be generically referred to as "chromium containing compound-N 2 -phosphinyl formamidine catalyst systems.”
- the chromium containing compound-N 2 -phosphinyl formamidine catalyst systems can be an ethylene trimerization catalyst system wherein the oligomer product (or trimerization product) comprises at least 70 wt.% hexenes; or a trimerization and tetramerization catalyst system wherein the oligomer product (or trimerization and tetramerization product) comprises at least 70 wt.% hexenes and octenes.
- the chromium containing compound of the catalyst system or the chromium containing compound of the chromium containing compound complexed to an N 2 -phosphinyl formamidine compound of the catalyst system can comprise, or consist essentially of, a chromium halide, carboxylate, ⁇ -diketonate, hydrocarboxide, nitrate, or chlorate; alternatively, a chromium halide, carboxylate, hydrocarboxide, or ⁇ -diketonate; alternatively, a chromium halide; alternatively, a chromium carboxylate; alternatively, a chromium hydrocarboxide; or alternatively, chromium ⁇ -diketonate.
- the alkylaluminum compound can comprise, or consist essentially of, a trialkylaluminum compound, an alkylaluminum halide (e.g., a dialkylaluminum halide, an alkylaluminum dihalide, and/or an alkylaluminum sesquihalide), an alkylaluminum alkoxide, an aluminoxane, or combinations thereof; or alternatively, an aluminoxane.
- an alkylaluminum halide e.g., a dialkylaluminum halide, an alkylaluminum dihalide, and/or an alkylaluminum sesquihalide
- an alkylaluminum alkoxide e.g., an aluminoxane, or combinations thereof; or alternatively, an aluminoxane.
- the catalyst system can comprise i) a chromium containing compound, ii) an N 2 -phosphinyl guanidine compound, and iii) an alkylaluminum compound; or alternatively, i) a chromium containing compound complexed to an N 2 -phosphinyl guanidine compound, and ii) an alkylaluminum compound.
- the catalyst systems using an N 2 -phosphinyl guanidine compound can be generically referred to as "chromium containing compound-N 2 -phosphinyl guanidine catalyst systems.”
- the chromium containing compound-N 2 -phosphinyl guanidine catalyst systems can be an ethylene trimerization catalyst system wherein the oligomer product (or trimerization product) comprises at least 70 wt.% hexenes; or a trimerization and tetramerization catalyst system wherein the oligomer product (or trimerization and tetramerization product) comprises at least 70 wt.% hexenes and octenes.
- the chromium containing compound of the catalyst system or the chromium containing compound of the chromium containing compound complexed to an N 2 -phosphinyl guanidine compound of the catalyst system can comprise, can consist essentially of, or can be, a chromium halide, carboxylate, ⁇ -diketonate, hydrocarboxide, nitrate, or chlorate; alternatively, a chromium halide, carboxylate, hydrocarboxide, or ⁇ -diketonate; alternatively, a chromium halide; alternatively, a chromium carboxylate; alternatively, a chromium hydrocarboxide; or alternatively, chromium ⁇ -diketonate.
- the alkylaluminum compound can comprise, or consist essentially of, a trialkylaluminum compound, an alkylaluminum halide (e.g., a dialkylaluminum halide, an alkylaluminum dihalide, and/or an alkylaluminum sesquihalide), an alkylaluminum alkoxide, an aluminoxane, or combinations thereof; or alternatively, an aluminoxane.
- an alkylaluminum halide e.g., a dialkylaluminum halide, an alkylaluminum dihalide, and/or an alkylaluminum sesquihalide
- an alkylaluminum alkoxide e.g., an aluminoxane, or combinations thereof; or alternatively, an aluminoxane.
- the catalyst system can be prepared by contacting the catalyst system with hydrogen.
- hydrogen can be added to the reaction system to accelerate the reaction and/or increase catalyst system activity. If desired, hydrogen can also be added to suppress polymer production.
- a hydrogen partial pressure at which the oligomer product can be formed can range from 2 psi to 100 psi; alternatively, 5 psi to 75 psi; or alternatively, 10 psi to 50 psi.
- the catalyst system can be prepared in an optional catalyst system solvent.
- the oligomer product can be formed in an optional reaction system diluent.
- the catalyst system solvent and reaction system diluent can be the same; or alternatively, the catalyst system solvent and reaction system diluent can be different.
- Catalyst system solvents and reaction system diluents are independently provided herein and can be utilized without limitation to further describe the optional catalyst system solvent utilized for preparing the catalyst system and the reaction system diluent in which the oligomer product can be formed.
- the compositions disclosed herein can be prepared by a process comprising a) contacting 1) ethylene, 2) the catalyst system comprising i) a chromium containing compound, ii) a heteroatomic ligand, and iii) an alkylaluminum compound, and 3) optionally a reaction system diluent; b) forming an oligomer product comprising 1-hexene and/or 1-octene in a reaction system; c) discharging a reaction system effluent from the reaction system; d) contacting the reaction system effluent with a catalyst system deactivating agent; and e) isolating the composition.
- the process can comprise a) contacting 1) ethylene, 2) the catalyst system comprising i) a chromium containing compound, ii) a heteroatomic ligand, and iii) an alkylaluminum compound, and 3) optionally a reaction system diluent; b) forming an oligomer product comprising 1-hexene and/or 1-octene in a reaction system; c) discharging a reaction system effluent from the reaction system; d) contacting the reaction system effluent with a catalyst system deactivating agent; and e) isolating a composition comprising (a) at least 76 mol%, at least 78 mol%, at least 80 mol%, or at least 82 mol% C 10 monoolefins, the C 10 monoolefins comprising (i) at least 3 mol%, at least 4 mol%, at least 5 mol%, at least 6 mol%, at least 7 mol%
- the process can comprise a) contacting 1) ethylene, 2) the catalyst system comprising i) a chromium containing compound, ii) a heteroatomic ligand, and iii) an alkylaluminum compound, and 3) optionally a reaction system diluent; b) forming an oligomer product comprising 1-hexene and/or 1-octene in a reaction system; c) discharging a reaction system effluent from the reaction system; d) contacting the reaction system effluent with a catalyst system deactivating agent; and e) isolating a composition comprising at least 95 mol%, at least 96 mol%, at least 97 mol%, at least 98 mol%, or at least 99 mol% C 10 monoolefins, the C 10 monoolefins comprising (i) at least 3 mol%, at least 4 mol%, at least 5 mol%, at least 6 mol%, or at
- the process can comprise a) contacting 1) ethylene, 2) the catalyst system comprising i) a chromium containing compound, ii) a heteroatomic ligand, and iii) an alkylaluminum compound, and 3) optionally a reaction system diluent; b) forming an oligomer product comprising 1-hexene and/or 1-octene in a reaction system; c) discharging a reaction system effluent from the reaction system; d) contacting the reaction system effluent with a catalyst system deactivating agent; e) isolating a first composition comprising (a) at least 76 mol%, at least 78 mol%, at least 80 mol%, or at least 82 mol% C 10 monoolefins, the C 10 monoolefins comprising (i) at least 3 mol%, at least 4 mol%, at least 5 mol%, at least 6 mol%, at least 7 mol
- these processes can further comprise forming a catalyst system mixture comprising, or consisting essentially of, i) a chromium containing compound, ii) a heteroatomic ligand, iii) an alkylaluminum compound, and iv) a catalyst system solvent; or alternatively, forming a catalyst system mixture comprising, or consisting essentially of, i) a heteroatomic ligand complexed to a chromium containing compound, ii) an alkylaluminum compound, and iii) a catalyst system solvent.
- the process further comprises forming a catalyst system mixture, the catalyst system mixture is contacted with ethylene, and the optional reaction system diluent.
- the step of contacting the catalyst system (or catalyst system mixture) with ethylene and the optional reaction system diluent can be a step of contacting the catalyst system (or catalyst system mixture) with ethylene, an optional reaction system diluent, and hydrogen.
- the catalyst system, chromium containing compound, a heteroatomic ligand, alkylaluminum compound, ethylene, solvents, are independently described herein and can be utilized, without limitation to further describe the processes for forming the first composition and/or second composition.
- the reaction system can operate at any pressure that can facilitate the formation of the oligomer product (or trimerization product, or ethylene tetramerization product, or trimerization and tetramerization product).
- the pressure at which the reaction system can operate can be any pressure that produces a desired oligomer product (or trimerization product, or tetramerization product, or trimerization and tetramerization product).
- the oligomer product (or trimerization product, or tetramerization product, or trimerization and tetramerization product) can be formed at a pressure greater than or equal to 0 psig (0 KPa); alternatively, greater than or equal to 50 psig (344 KPa); alternatively, greater than or equal to 100 psig (689 KPa); or alternatively, greater than or equal to 150 psig (1.0 MPa).
- the oligomer product (or trimerization product, or tetramerization product, or trimerization and tetramerization product) can be formed at a pressure ranging from 0 psig (0 KPa) to 2,500 psig (17.3 MPa); alternatively, from 0 psig (KPa) to 1,600 psig (11.0 MPa); alternatively, from 0 psig (KPa) to 1,500 psig (10.4 MPa); alternatively, from 50 psig (344 KPa) to 2,500 psig (17.3 MPa); alternatively, from 100 psig (689 KPa) to 2,500 psig (17.3 MPa); alternatively, from 150 psig (1.0 MPa) to 2,000 psig (13.8 MPa); or alternatively, from 300 psig (2.0 MPa) to 900 psig (6.2 MPa).
- the ethylene pressure (or ethylene partial pressure) at which the oligomer product (or trimerization product, or tetramerization product, or trimerization and tetramerization product) can be formed can be greater than or equal to 0 psig (0 KPa); alternatively, greater than or equal to 50 psig (344 KPa); alternatively, greater than or equal to 100 psig (689 KPa); or alternatively, greater than or equal to 150 psig (1.0 MPa).
- the ethylene pressure (or ethylene partial pressure) at which the oligomer product (or trimerization product, or tetramerization product, or trimerization and tetramerization product) can be formed can range from 0 psig (0 KPa) to 2,500 psig (17.3 MPa); alternatively, from 50 psig (344 KPa) to 2,500 psig (17.3 MPa); alternatively, from 100 psig (689 KPa) to 2,500 psig (17.3 MPa); or alternatively, from 150 psig (1.0 MPa) to 2,000 psig (13.8).
- a temperature (e.g., a minimum temperature) at which the oligomer product (or trimerization product, or tetramerization product, or trimerization and tetramerization product) can be formed can be at least 0 °C; alternatively, at least 10 °C; alternatively, at least 20 °C; alternatively, at least 30 °C; alternatively, at least 40 °C; alternatively, at least 50 °C; alternatively, at least 60 °C; alternatively, at least 70 °C; alternatively, at least 80 °C; alternatively, at least 90 °C; alternatively, at least 100 °C; alternatively, at least 110 °C; alternatively, at least 120 °C; alternatively, at least 130 °C; alternatively, at least 140 °C; alternatively, at least 150 °C; alternatively, at least 160 °C; alternatively, at least 170 °C; or alternatively, at least 180 °C.
- a temperature (e.g., maximum temperature) at which the oligomer product (or trimerization product, or tetramerization product, or trimerization and tetramerization product) can be formed can be less than 180 °C; alternatively, less than 160 °C; alternatively, less than 140 °C; alternatively, less than 120 °C; alternatively, less than 100 °C; alternatively, less than 90 °C; or alternatively, less than 80 °C.
- the temperature at which the oligomer product (or trimerization product, or tetramerization product, or trimerization and tetramerization product) can be formed can range from any minimum temperature described herein to any maximum reaction temperature described herein as long as the maximum temperature is greater than the minimum temperature.
- the temperature at which the oligomer product (or trimerization product, or ethylene tetramerization product, or trimerization and tetramerization product) can be formed can range from 0 °C to 180 °C; alternatively, from 10 °C to 160 °C; alternatively, from 20 °C to 140 °C; alternatively, from 30 °C to 120 °C; alternatively, from 40 °C to 100 °C; alternatively, from 50 °C to 100 °C; or alternatively, from 60 °C to 140 °C.
- Other temperature ranges at which the oligomer product (or trimerization product, or tetramerization product, or trimerization and tetramerization product) can be formed can be understood by those skilled in the art with the help of this disclosure.
- a reaction time can comprise any time that can produce a desired quantity of oligomer product (or trimerization product, or tetramerization product, or trimerization and tetramerization product); alternatively, any time that can provide a desired catalyst system productivity; or alternatively, any time that can provide a desired conversion of ethylene.
- an ethylene conversion can be at least 30 wt.% percent; alternatively, at least 35 wt.% percent; alternatively, at least 40 wt.% percent; or alternatively, at least 45 wt.% percent.
- the oligomer product (or trimerization product) can comprise at least 70 wt.% hexene; alternatively, at least 75 wt.% hexene; alternatively, at least 80 wt.% hexene; alternatively, at least 85 wt.% hexene; or alternatively, at least 90 wt.% hexene, based upon the weight of the oligomer product (or trimerization product).
- the oligomer product (or trimerization product) can comprise from 70 wt.% to 99.8 wt.% hexene; alternatively, from 75 wt.% to 99.7 wt.% hexene; or alternatively, from 80 wt.% to 99.6 wt.% hexane, based upon the weight of the oligomer product (or trimerization product).
- the oligomer product (or tetramerization product) can comprise at least 70 wt.% octene; alternatively, at least 75 wt.% octene; alternatively, at least 80 wt.% octene; alternatively, at least 85 wt.% octene; or alternatively, at least 90 wt.% octene, based upon the weight of the oligomer product (or tetramerization product).
- the oligomer product (or tetramerization product) can comprise from 70 wt.% to 99.8 wt.% octene; alternatively, from 75 wt.% to 99.7 wt.% octene; or alternatively, from 80 wt.% to 99.6 wt.% octene, based upon the weight of the oligomer product (or tetramerization product).
- the oligomer product (or trimerization and tetramerization product) can comprise at least 70 wt.% hexene and octene; alternatively, at least 75 wt.% hexene and octene; alternatively, at least 80 wt.% hexene and octene; alternatively, at least 85 wt.% hexene and octene; or alternatively, at least 90 wt.% hexene and octene, based upon the weight of the oligomer product (or trimerization and tetramerization product).
- the oligomer product (or trimerization and tetramerization product) can comprise from 70 wt.% to 99.8 wt.% hexene and octene; alternatively, from 75 wt.% to 99.7 wt.% hexene and octene; or alternatively, from 80 wt.% to 99.6 wt.% hexene and octene, based upon the weight of the oligomer product (or trimerization and tetramerization product).
- the oligomer product (or trimerization product, tetramerization product, or trimerization and tetramerization product) can further comprise the C 10 monoolefins (as described herein) which can be present in the compositions comprising at least 76 mol%, at least 78 mol%, at least 80 mol%, or at least 82 mol% C 10 monoolefins; or alternatively, the compositions comprising at least 95 mol%, at least 96 mol%, at least 97 mol%, at least 98 mol%, or at least 99 mol% C 10 monoolefins.
- the C 10 monoolefins as described herein
- the oligomer product (or trimerization product, tetramerization product, or trimerization and tetramerization product) can further comprise the C 9- monoolefins (as described herein) and/or the C 11+ monoolefins (as described herein) which can be present in the compositions comprising at least 76 mol%, at least 78 mol%, at least 80 mol%, or at least 82 mol% C 10 monoolefins; or alternatively, the compositions comprising at least 95 mol%, at least 96 mol%, at least 97 mol%, at least 98 mol%, or at least 99 mol% C 10 monoolefins.
- the trimer can comprise at least 85 wt.% 1-hexene; alternatively, at least 87.5 wt.% 1-hexene; alternatively, at least 90 wt.% 1-hexene; alternatively, at least 92.5 wt.% 1-hexene; alternatively, at least 95 wt.% 1-hexene; alternatively, at least 97 wt.% 1-hexene; or alternatively, at least 98 wt.% 1-hexene, based upon the weight of the trimer.
- the trimer can comprise from 85 wt.% to 99.9 wt.% 1-hexene; alternatively, from 87.5 wt.% to 99.9 wt.% 1-hexene; alternatively, from 90 wt.% to 99.9 wt.% 1-hexene; alternatively, from 92.5 wt.% to 99.9 wt.% 1-hexene; alternatively, from 95 wt.% to 99.9 wt.% 1-hexene; alternatively, from 97 wt.% to 99.9 wt.% 1-hexene; or alternatively, from 98 wt.% to 99.9 wt.% 1-hexene, based upon the weight of the trimer.
- the tetramer can comprise at least 85 wt.% 1-octene; alternatively, at least 87.5 wt.% 1-octene; alternatively, at least 90 wt.% 1-octene; alternatively, at least 92.5 wt.% 1-octene; alternatively, at least 95 wt.% 1-octene; alternatively, at least 97 wt.% 1-octene; or alternatively at least 98 wt.% 1-octene, based upon the weight of the tetramer.
- the tetramer can comprise from 85 wt.% to 99.9 wt.% 1-octene; alternatively, from 87.5 wt.% to 99.9 wt.% 1-octene; alternatively, from 90 wt.% to 99.9 wt.% 1-octene; alternatively, from 92.5 wt.% to 99.9 wt.% 1-octene; alternatively, from 95 wt.% to 99.9 wt.% 1-octene; alternatively, from 97 wt.% to 99.9 wt.% 1-octene; or alternatively, from 98 wt.% to 99.9 wt.% 1-octene, based upon the weight of the tetramer.
- reaction system effluent generally refers to all the material which exits the reaction system through a reaction system outlet/discharge, which discharges a reaction mixture and can include reaction mixture (e.g., ethylene, catalyst system or catalyst system components, and/or optional reaction system diluent or solvent), and/or reaction product(s) (e.g., oligomerization product including oligomers and non-oligomers).
- reaction mixture e.g., ethylene, catalyst system or catalyst system components, and/or optional reaction system diluent or solvent
- reaction product(s) e.g., oligomerization product including oligomers and non-oligomers
- reaction system effluent and its derivatives can be qualified to refer to certain portions by use of additional qualifying terms.
- reaction system effluent refers to all material which exits the reaction system through the reaction system outlet/discharge
- reaction system oligomerization product effluent refers to only the oligomerization product within the reaction system effluent.
- the reaction system effluent can comprise an oligomer product comprising at least 60 mol%; at least 65 mol%; at least 70 mol%; at least 75 mol%; or at least 80 mol% 1-hexene and/or 1-octene, the catalyst system, and the optional reaction system diluent.
- the reaction system effluent can comprise i) an oligomer product comprising at least 60 mol%, at least 65 mol%, at least 70 mol%, at least 75 mol%, or at least 80 mol% 1-hexene, ii) the catalyst system, and iii) the optional reaction system diluent.
- the reaction system effluent can comprise i) an oligomer product comprising at least 60 mol%, at least 65 mol%, at least 70 mol%; at least 75 mol%, or at least 80 mol% 1-octene, ii) the catalyst system, and iii) the optional reaction system diluent.
- the reaction system effluent can comprise i) an oligomer product comprising at least 60 mol%, at least 65 mol%, at least 70 mol%, at least 75 mol%, or at least 80 mol% 1-hexene and 1-octene, ii) the catalyst system, and iii) the optional reaction system diluent.
- the reaction system effluent can further comprise the C 10 monoolefins (as described herein) which can be present in the compositions comprising at least 76 mol%, at least 78 mol%, at least 80 mol%, or at least 82 mol% C 10 monoolefins; or alternatively, the compositions comprising at least 95 mol%, at least 96 mol%, at least 97 mol%, at least 98 mol%, or at least 99 mol% C 10 monoolefins.
- the C 10 monoolefins as described herein
- reaction system effluent can further comprise the C 9- monoolefins (as described herein) and/or the C 11+ monoolefins (as described herein) which can be present in the compositions comprising at least 76 mol%, at least 78 mol%, at least 80 mol%, or at least 82 mol% C 10 monoolefins; or alternatively, the compositions comprising at least 95 mol%, at least 96 mol%, at least 97 mol%, at least 98 mol%, or at least 99 mol% C 10 monoolefins.
- reaction system effluent can be treated and subjected to one or more separation processes to recover components from the reaction system effluent (e.g., unreacted ethylene, solvent, oligomer product(s), and/or by-product(s), among others).
- components e.g., unreacted ethylene, solvent, oligomer product(s), and/or by-product(s), among others.
- the reaction system effluent Prior to recovery of the trimer, tetramer, or trimer and tetramer, the reaction system effluent can be contacted with a catalyst system deactivating and quench agent (alternatively, referred to herein as a "catalyst system kill agent") to deactivate and quench the active catalyst system (e.g., to form a deactivated and quenched reaction system effluent).
- a catalyst system deactivating and quench agent alternatively, referred to herein as a "catalyst system kill agent
- the reaction system effluent can be contacted with a catalyst system deactivating agent to at least partially deactivate the catalyst system and produce a deactivated catalyst system (e.g., to form a deactivated reaction system effluent, or alternatively a reaction system effluent containing a deactivated catalyst system); and then at least a portion of the reaction system effluent containing the deactivated catalyst system or deactivated catalyst system components can be contacted with a catalyst system quench agent to quench the catalyst system.
- the catalyst system deactivating and quench agent, catalyst system deactivating agent, and/or catalyst system quench agent can be independently selected from monoalcohols, diols, polyols, or combinations thereof.
- the catalyst system deactivating and quench agent, catalyst system deactivating agent, and/or catalyst system quench agent can comprise any mono-alcohol, diol, or polyol which is soluble in the reaction system effluent.
- the mono-alcohol, diol, or polyol can be selected by boiling point, molecular weight, and/or such that the mono-alcohol, diol, or polyol does not form an azeotrope with the oligomer(s), trimer, and/or tetramer (and/or reaction system solvent).
- the mono-alcohol, diol, or polyol can have a boiling point different from the oligomer(s), trimer, and/or tetramer (and/or reaction system solvent) in the reaction system effluent.
- the mono-alcohol can be a C 4 to C 30 mono-alcohol, alternatively, a C 4 to C 20 mono-alcohol, or alternatively, a C 4 to C 12 mono-alcohol.
- the mono-alcohol can be selected to be easily removable from the oligomer(s), trimer, or tetramer (e.g., 1-hexene in an ethylene trimerization process).
- Non-limiting examples of monoalcohols suitable for use in the present disclosure include 1-hexanol, 2-hexanol, 3-hexanol, 2-ethyl-1-hexanol, 1-heptanol, 2-heptanol, 3-heptanol, 4-heptanol, 2-methyl-3-heptanol, 1-octanol, 2-octanol, 3-octanol, 4-octanol, 7-methyl-2-decanol, 1-decanol, 2-decanol, 3-decanol, 4-decanol, 5-decanol, 2-ethyl-1-decanol, or combinations thereof.
- the mono-alcohol can comprise 2-ethyl-1-hexanol.
- the catalyst system deactivating and quench agent can be contacted with the reaction system effluent in an amount sufficient to deactivate the catalyst system (i.e., an amount that can inhibit, or halt: (1) production of undesirable solids, i.e., polymer; and/or (2) oligomer(s), trimer, and/or tetramer product purity degradation due to isomerization) in subsequent product separation processes and quench the catalyst system (i.e., an amount that can inhibit a pyrophoric nature of residual catalyst components).
- the catalyst system deactivating and quench agent can be contacted with the reaction system effluent at an alcohol to metal of the metal alkyl compound (including metal alkyl compound which can be designated as a halogen containing compound) molar ratio (also referred to as an alcohol to metal molar ratio) of up to 100:1; alternatively, up to 50:1; alternatively, up to 25:1; alternatively, up to 10:1; alternatively, up to 5:1; alternatively, from 0.01:1 to 100:1; alternatively, from 0.1:1 to 50:1; alternatively, from 0.5:1 to 25:1; alternatively, from 0.75:1 to 5:1; alternatively, from 1:1 to 4:1; or alternatively, from 2:1 to 3:1.
- Catalyst system deactivation and quench processes are described in more detail in U.S. Patent Nos. 5,689,028 and US 8,344,198 , among other documents.
- the reaction system effluent can be contacted with a catalyst system deactivation agent to at least partially deactivate the catalyst system; and later, a portion of the reaction system effluent containing at least a portion of the deactivated catalyst system (e.g., a portion of the reaction system effluent remaining after separating the oligomer, trimer, tetramer, and/or reaction system solvent from a reaction system effluent stream containing at least a portion of the at least partially deactivated catalyst system) can be contacted with the catalyst system quench agent to quench the catalyst system.
- a portion of the reaction system effluent containing at least a portion of the deactivated catalyst system e.g., a portion of the reaction system effluent remaining after separating the oligomer, trimer, tetramer, and/or reaction system solvent from a reaction system effluent stream containing at least a portion of the at least partially deactivated catalyst system
- the catalyst system quench agent can quench
- the catalyst system deactivating agent can be contacted with the reaction system effluent at a catalyst deactivating agent to metal of the metal alkyl compound (including metal alkyl compound which can be designated as a halogen containing compound) molar ratio of from 0.75:1 to 1.25:1; alternatively, from 0.8:1 to 1.2:1; alternatively, from 0.85:1 to 1.15:1; or alternatively, about 1:1.
- metal alkyl compound including metal alkyl compound which can be designated as a halogen containing compound
- the catalyst system quench agent can be contacted with at least a portion of a stream containing at least a portion of the at least partially deactivated catalyst system at a catalyst system quench agent to metal of the metal alkyl compound (including metal alkyl compound which can be designated as a halogen containing compound) molar ratio of from 0.5:1 to 1.5:1; alternatively, from 0.7:1 to 1.2:1; alternatively, from 0.8:1 to 1.1:1; or alternatively, about 1:1. Additional information regarding a split catalyst system deactivation and catalyst system quench can be found in U.S. Patent No. 8,049,052 .
- the reaction system effluent can comprise components present in the reaction mixture, as previously discussed herein.
- the reaction system effluent can generally include ethylene, the oligomer product (or alternatively, trimerization product, tetramerization product, or trimerization and tetramerization product), the catalyst system (including a chromium containing compound which may or may not be in the same form as the chromium containing compound contacted to form the catalyst system), and/or the reaction system solvent, among other components (e.g., the C 10 monoolefins of the first composition or second composition as described herein).
- a deactivated reaction system effluent or deactivated and quenched reaction system effluent generally represents the reaction system effluent which has been contacted with the catalyst system deactivating agent or the catalyst system deactivating and quench agent, respectively; and generally comprises ethylene, the oligomer product (or alternatively, trimerization product, tetramerization product, or trimerization and tetramerization product), the deactivated catalyst system or the deactivated and quenched catalyst system (including a chromium containing compound, and other deactivated quenched catalyst system components or deactivated and quenched catalyst system components), and/or the reaction system solvent, among other components.
- the chromium containing compound may be the same as (or alternatively, may not be in the same form as) the chromium containing compound present in the catalyst system prior to the oligomerization reaction
- the term "chromium containing compound" and their derivatives when used in regards to the reaction system effluent, deactivated reaction system effluent, or deactivated and quenched reaction system effluent, refers to all chromium containing compounds, regardless of form, that are present in the reaction system effluent, deactivated reaction system effluent, deactivated and quenched reaction system effluent, or reaction system effluent stream (deactivated, or deactivated and quenched) which has been processed to remove one or more materials comprising all or a portion of ethylene, the oligomerization product (or alternatively, ethylene trimerization product
- chromium containing compounds when used in regards to the reaction system effluent, deactivated reaction system effluent, or deactivated and quenched reaction system effluent, refers to the chromium containing compounds which are used to form the catalyst system or refer to the chromium containing compound complexed to a heteroatomic ligand of the catalyst system.
- the oligomer(s), trimer, tetramer, trimer and tetramer, and/or reaction system solvent can be separated (e.g., isolated) from a deactivated reaction system effluent or deactivated and quenched reaction system effluent. Any separation process or combination of processes can be used, including, for example, distillation.
- the separation process can comprise at least one separation vessel comprising columns, tanks, flash vessels, distillation columns, or combinations thereof.
- the oligomer(s) can be isolated from a deactivated reaction system effluent or deactivated and quenched reaction system effluent to yield a stream (e.g., isolated stream) comprising (a) at least 90 mol% 1-hexene; alternatively, at least 92.5 wt.% 1-hexene; alternatively, at least 95 wt.% 1-hexene; alternatively, at least 97 wt.% 1-hexene; or alternatively, at least 98 wt.% 1-hexene, based upon the weight of the stream; (b) at least 90 mol% 1-octene; alternatively, at least 92.5 wt.% 1-octene; alternatively, at least 95 wt.% 1-octene; alternatively, at least 97 wt.% 1-octene; or alternatively
- the isolated stream can comprise from 90 wt.% to 99.9 wt.% 1-hexene; alternatively, from 92.5 wt.% to 99.9 wt.% 1-hexene; alternatively, from 95 wt.% to 99.9 wt.% 1-hexene; alternatively, from 97 wt.% to 99.9 wt.% 1-hexene; or alternatively, from 98 wt.% to 99.9 wt.% 1-hexene, based upon the weight of the isolated stream.
- the isolated stream can comprise from 90 wt.% to 99.9 wt.% 1-octene; alternatively, from 92.5 wt.% to 99.9 wt.% 1-octene; alternatively, from 95 wt.% to 99.9 wt.% 1-octene; alternatively, from 97 wt.% to 99.9 wt.% 1-octene; or alternatively, from 98 wt.% to 99.9 wt.% 1-octene, based upon the weight of the isolated stream.
- the isolated stream can comprise from 90 wt.% to 99.9 wt.% 1-hexene and 1-octene; alternatively, from 92.5 wt.% to 99.9 wt.% 1-hexene and 1-octene; alternatively, from 95 wt.% to 99.9 wt.% 1-hexene and 1-octene; alternatively, from 97 wt.% to 99.9 wt.% 1-hexene and 1-octene; or alternatively, from 98 wt.% to 99.9 wt.% 1-hexene and 1-octene, based upon the weight of the isolated stream.
- the process(es) for isolating the oligomer(s) can also isolate a composition (e.g., a first composition) comprising (a) at least 76 mol%, at least 78 mol%, at least 80 mol%, or at least 82 mol% C 10 monoolefins, the C 10 monoolefins comprising (i) at least 3 mol%, at least 4 mol%, at least 5 mol%, at least 6 mol%, at least 7 mol%, or at least 8 mol% 2-butyl-1-hexene, (ii) at least 8 mol%, at least 9 mol%, at least 10 mol%, at least 11 mol%, at least 12 mol%, or at least 13 mol%
- a composition (e.g., a second composition) can be isolated from a deactivated reaction system effluent or deactivated and quenched reaction system effluent, or can be recovered (e.g., isolated, separated, etc.) from the first composition, the second composition comprising at least 95 mol%, at least 96 mol%, at least 97 mol%, at least 98 mol%, or at least 99 mol% C 10 monoolefins, the C 10 monoolefins comprising (i) at least 3 mol%, at least 4 mol%, at least 5 mol%, at least 6 mol%, or at least 7 mol% 2-butyl-1-hexene, (ii) at least 10 mol%, at least 11 mol%, at least 12 mol%, at least 13 mol%, or at least 14 mol% 3-propyl-1-heptene, (iii) at least 7 mol%, at least 8 mol%, at least 9
- compositions comprising C 10 monoolefins as disclosed herein were isolated from an ethylene trimerization process (e.g., a commercial ethylene trimerization plant) utilizing a chromium pyrrole catalyst system.
- the compositions comprising C 10 monoolefins were analyzed by gas chromatograph-mass spectrometry (GC-MS) using a 15 m x 0.25 mm x 0.5 ⁇ m DB-5 column and/or a 40 m x 0.1 mm x 0.1 ⁇ m DB-1 column to determine component identities, and standard gas chromatography (GC) using a 60 m x 0.32 mm x 1 ⁇ m DB-1 column to determine the quantity of the components present in the compositions.
- GC-MS gas chromatograph-mass spectrometry
- Table 3 The data and analysis of the compositions from the commercial ethylene trimerization plant are provided in Table 3, Table 4, and Table 5.
- Table 3 provides the component identities for the hydrocarbon components present in an amount of at least 0.03 wt.%, and identified heteroatomic compounds present in at least 0.1 wt.%, which were then converted to mol%.
- Table 4 provides a compositional make-up of the composition in terms of aliphatic hydrocarbon carbon number, aromatic hydrocarbon, and alcohol of the compositions isolated from the commercial ethylene trimerization plant.
- Table 5 provides the distribution of decene in the composition isolated from the commercial ethylene trimerization plant.
- Embodiment 1 A composition comprising: a) at least 76 mol%, at least 78 mol%, at least 80 mol%, or at least 82 mol% C 10 monoolefins, the C 10 monoolefins comprising i) at least 3 mol%, at least 4 mol%, at least 5 mol%, at least 6 mol%, at least 7 mol%, or at least 8 mol% 2-butyl-1-hexene, ii) at least 8 mol%, at least 9 mol%, at least 10 mol%, at least 11 mol%, at least 12 mol%, or at least 13 mol% 3-propyl-1-heptene, iii) at least 6 mol%, at least 7 mol%, at least 8 mol%, at least 9 mol%, at least 10 mol%, or at least 11 mol% 4-ethyl-1-octene, and iv) at least 20 mol%, at least 22 mol%
- Embodiment 2 The composition of embodiment 1 or 2, wherein the composition comprises from 76 mol% to 92 mol%, from 78 mol% to 90 mol%, from 80 mol% to 88 mol%, or from 82 mol% to 86 mol% C 10 monoolefins.
- Embodiment 3 The composition of embodiment 1 or 2, wherein the composition comprises from 1 mol% to 12 mol%, from 2 mol% to 10 mol%, from 3 mol% to 8 mol%, or from 4 mol% to 7 mol% C 14 monoolefins.
- Embodiment 4 The composition of any one of embodiments 1 to 3, further comprising from 0.1 mol% to 5 mol%, from 0.25 mol% to 4 mol%, or from 0.5 mol% to 3 mol% C 12 monoolefins, the C 12 monoolefins comprising from 54 mol% to 74 mol%, from 56 mol% to 72 mol%, from 58 mol% to 70 mol%, or from 60 mol% to 68 mol% 1-dodecene.
- Embodiment 5 The composition of embodiment 1 or 4, further comprising from 0.1 mol% to 5 mol%, from 0.25 mol% to 4 mol%, or from 0.5 mol% to 3 mol% C 8 monoolefins, the C 8 monoolefins comprising at least 95 mol%, at least 96 mol%, at least 97 mol%, at least 98 mol%, or at least 99 mol% 1-octene.
- Embodiment 6 The composition of any one of embodiments 1 to 5, further comprising from 0.05 mol% to 2 mol%, from 0.04 mol% to 1.5 mol%, from 0.06 mol% to 1.25 mol%, from 0.08 mol% to 1 mol%, or from 0.1 mol% to 0.75 mol% C 16 monoolefins and/or C 18 monoolefins.
- Embodiment 7 The composition of any one of embodiments 1 to 6, further comprising from 0.2 mol% to 6 mol%, from 0.3 mol% to 4 mol%, from 0.4 mol% to 2 mol%, or from 0.5 mol% to 1.5 mol% acyclic saturated hydrocarbons.
- Embodiment 8 The composition of embodiment 7, wherein the acyclic saturated hydrocarbons comprise octane, decane, dodecane, tetradecane, or combinations thereof.
- Embodiment 9 The composition of embodiment 7 or 8, wherein the acyclic saturated hydrocarbons comprise a) from 10 mol% to 26 mol%, from 12 mol% to 24 mol%, or from 14 mol% to 22 mol% octane, b) from 24 mol% to 48 mol%, from 27 mol% to 45 mol%, or from 30 mol% to 42 mol% decane, c) from 22 mol% to 40 mol%, from 24 mol% to 38 mol%, or from 26 mol% to 36 mol% dodecane, and d) from 7 mol% to 23 mol%, from 9 mol% to 21 mol%, or from 11 mol% to 19 mol% tetradecane.
- Embodiment 10 The composition of any one of embodiments 1 to 9, further comprising from 1.9 mol% to 5.1 mol%, from 2.1 mol% to 4.9 mol%, from 2.3 mol% to 4.7 mol%, or from 2.5 mol% to 4.5 mol% cyclic saturated hydrocarbons.
- Embodiment 11 The composition of embodiment 10, wherein the cyclic saturated hydrocarbon is methylcyclopentane, cyclohexane, methylcyclohexane, or combinations thereof.
- Embodiment 12 The composition of any one of embodiments 1 to 11, further comprising from 1 mol% to 3.4 mol%, from 1.2 mol% to 3.2 mol%, from 1.4 mol% to 3.0 mol%, or from 1.6 mol% to 2.8 mol% of a C 6 to C 12 aromatic hydrocarbon.
- Embodiment 13 The composition of embodiment 12, wherein the C 6 to C 12 aromatic hydrocarbon is benzene, toluene, ethylbenzene, xylene, mesitylene, hexamethylbenzene, or combinations thereof.
- Embodiment 14 The composition of any one of embodiments 1 to 13, further comprising from 0.4 mol% to 3 mol%, from 0.6 mol% to 3 mol%, from 0.8 mol% to 2.5 mol%, or from 1 mol% to 2 mol% of a C 4 to C 12 alcohol.
- Embodiment 15 The composition of embodiment 14, wherein the C 4 to C 12 alcohol is 1-hexanol, 2-hexanol, 3-hexanol, 2-ethyl-1-hexanol, 1-heptanol, 2-heptanol, 3-heptanol, 4-heptanol, 2-methyl-3-heptanol, 1-octanol, 2-octanol, 3-octanol, 4-octanol, 7-methyl-2-decanol, 1-decanol, 2-decanol, 3-decanol, 4-decanol, 5-decanol, 2-ethyl-1-decanol, or combinations thereof.
- Embodiment 16 A composition comprising at least 95 mol%, at least 96 mol%, at least 97 mol%, at least 98 mol%, or at least 99 mol% C 10 monoolefins, the C 10 monoolefins comprising i) at least 3 mol%, at least 4 mol%, at least 5 mol%, at least 6 mol%, or at least 7 mol% 2-butyl-1-hexene, ii) at least 10 mol%, at least 11 mol%, at least 12 mol%, at least 13 mol%, or at least 14 mol% 3-propyl-1-heptene, iii) at least 7 mol%, at least 8 mol%, at least 9 mol%, at least 10 mol%, or at least 11 mol% 4-ethyl-1-octene, and iv) at least 24 mol%, at least 26 mol%, at least 28 mol%, at least 30 mol%, or at least
- Embodiment 17 The composition of embodiment 16, wherein the composition comprises less than 3 mol%, less than 2.5 mol%, less than 2 mol%, less than 1.5 mol%, less than 1 mol%, or less than 0.5 mol% C 9- hydrocarbons.
- Embodiment 18 The composition of embodiment 15 or 16, wherein composition comprises less than 3 mol%, less than 2.5 mol%, less than 2 mol%, less than 1.5 mol%, less than 1 mol%, or less than 0.5 mol% C 11+ hydrocarbons.
- Embodiment 19 The composition of any one of embodiments 1 to 15, or the composition of any one of embodiments 14 to 18, wherein the C 10 monoolefins comprise from 3 mol% to 20 mol%, from 4 mol% to 18 mol%, from 5 mol% to 17 mol%, from 6 mol% to 16 mol%, or from 7 mol% to 15 mol% 2-butyl-1-hexene.
- Embodiment 20 The composition of any one of embodiments 1 to 15, or the composition of any one of embodiments 14 to 19, wherein the C 10 monoolefins comprise from 10 mol% to 32 mol%, from 11 mol% to 30 mol%, from 12 mol% to 28 mol%, from 13 mol% to 26 mol%, or from 14 mol% to 24 mol% 3-propyl-1-heptene.
- Embodiment 21 The composition of any one of embodiments 1 to 15, or the composition of any one of embodiments 16 to 20, wherein the C 10 monoolefins comprise from 7 mol% to 25 mol%, from 8 mol% to 24 mol%, from 9 mol% to 23 mol%, from 10 mol% to 22 mol%, or from 11 mol% to 21 mol% 4-ethyl-1-octene.
- Embodiment 22 The composition of any one of embodiments 1 to 15, or the composition of any one of embodiments 16 to 21, wherein the C 10 monoolefins comprise from 24 mol% to 52 mol%, from 26 mol% to 50 mol%, from 28 mol% to 48 mol%, from 30 mol% to 46 mol%, or from 32 mol% to 44 mol% 5-methyl-1-nonene.
- Embodiment 23 The composition of any one of embodiments 1 to 15, or the composition of any one of embodiments 16 to 22, wherein a molar ratio of 5-methyl-1-nonene to 2-butyl-1-hexene is at least 2:1, at least 2.4:1, at least 2.6:1, or at least 2.8:1.
- Embodiment 24 The composition of any one of embodiments 1 to 15 or the composition of any one of embodiments 16 to 23, wherein a molar ratio of 5-methyl-1-nonene to 3-propyl-1-heptene is at least 1.2:1, at least 1.4:1, at least 1.6:1, or at least 1.8:1.
- Embodiment 25 The composition of any one of embodiments 1 to 15 or the composition of any one of embodiments 16 to 24, wherein a molar ratio of 5-methyl-1-nonene to 4-ethyl-1-octene is at least 1.6:1, at least 1.7:1, at least 1.9:1, or at least 2.1:1.
- Embodiment 26 The composition of any one of embodiments 1 to 15 or the composition of any one of embodiments 16 to 25, wherein the C 10 monoolefins comprises from 1 mol% to 16 mol%, from 2 mol% to 15 mol%, from 3 mol% to 14 mol%, from 4 mol% to 13 mol%, or from 6 mol% to 12 mol% 4-decene and/or 5-decene.
- Embodiment 27 The composition of any one of embodiments 1 to 15 or the composition of any one of embodiments 16 to 26, wherein the C 10 monoolefins comprises less than or equal to 10 mol%, less than or equal to 9 mol%, less than or equal to 8 mol%, less than or equal to 7 mol%, or less than or equal to 6 mol% 1-decene.
- Embodiment 28 The composition of any one of embodiments 1 to 15 or the composition of any one of embodiments 16 to 27, wherein the C 10 monoolefins comprises from 0.5 mol% to 9 mol%, from 1 mol% to 8 mol%, from 1.5 mol% to 7 mol%, or from 2 mol% to 6 mol% 1-decene.
- Embodiment 29 A process comprising: a) contacting 1) ethylene, 2) a catalyst system comprising i) a chromium containing compound, ii) a heteroatomic ligand, and iii) an alkylaluminum compound, and 3) optionally a reaction system diluent; b) forming an oligomer product comprising 1-hexene and/or 1-octene in a reaction system; c) discharging a reaction system effluent from the reaction system; d) contacting the reaction system effluent with a catalyst system deactivating agent; and e) isolating the composition of any one of embodiments 1 to 15, or the composition of any one of embodiments 16 to 28.
- Embodiment 30 A process comprising: a) contacting 1) ethylene, 2) a catalyst system comprising i) a chromium containing compound, ii) a heteroatomic ligand, and iii) an alkylaluminum compound, and 3) optionally a reaction system diluent; b) forming an oligomer product comprising 1-hexene and/or 1-octene in a reaction system; c) discharging a reaction system effluent from the reaction system; d) contacting the reaction system effluent with a catalyst system deactivating agent; and e) isolating a first composition defined by any one of embodiments 1 to 15.
- Embodiment 31 The process of embodiment 30, the process further comprising recovering a second composition defined by any one of embodiments 16 to 28 from the first composition defined by any one of embodiments 1 to 15.
- Embodiment 32 The process of any one of embodiments 29 to 31, wherein the catalyst system is prepared in a catalyst system solvent.
- Embodiment 33 The process of embodiment 32, wherein the reaction system effluent comprises the oligomer product comprising at least 60 mol% 1-hexene and/or 1-octene, the catalyst system, and the optional reaction system diluent.
- Embodiment 34 The process of any one of embodiments 29 to 33, wherein the process further comprises isolating a stream comprising (a) at least 90 mol% 1-hexene, (b) at least 90 mol% 1-octene, or (c) at least 90 mol% 1-hexene and 1-octene.
- Embodiment 35 The process of any one of embodiments 29 to 34, wherein the heteroatomic ligand is a pyrrole compound, a diphosphino aminyl compound, an N 2 -phosphinyl amidine compound, an N 2 -phosphinyl formamidine compound, an N 2 -phosphinyl guanidine compound, or combinations thereof.
- the heteroatomic ligand is a pyrrole compound, a diphosphino aminyl compound, an N 2 -phosphinyl amidine compound, an N 2 -phosphinyl formamidine compound, an N 2 -phosphinyl guanidine compound, or combinations thereof.
- Embodiment 36 The process of any one of embodiments 29 to 35, wherein the catalyst system is selected from the group consisting of a) a chromium containing compound, a pyrrole compound, an alkylaluminum compound, and optionally a halide containing compound; b) a chromium containing compound, a diphosphino aminyl compound, an alkylaluminum compound; c) a chromium containing compound complexed to a diphosphino aminyl compound, and an alkylaluminum compound; d) a chromium containing compound, an N 2 -phosphinyl amidine compound, and an alkylaluminum compound; e) a chromium containing compound complexed to an N 2 -phosphinyl amidine compound, and an alkylaluminum compound; f) a chromium containing compound, an N 2 -phosphinyl formamidine compound, an alkylalum
- a first embodiment which is a composition comprising: a) at least 76 mol% C 10 monoolefins, the C 10 monoolefins comprising i) at least 3 mol% 2-butyl-1-hexene, ii) at least 8 mol% 3-propyl-1-heptene, iii) at least 6 mol% 4-ethyl-1-octene, and iv) at least 20 mol% 5-methyl-1-nonene; and b) at least 1 mol% C 14 monoolefins.
- a second embodiment which is the composition of the first embodiment, wherein the C 10 monoolefins comprise i) from 3 mol% to 20 mol% 2-butyl-1-hexene, ii) from 10 mol% to 32 mol% 3-propyl-1-heptene, iii) from 7 mol% to 25 mol% 4-ethyl-1-octene, and iv) from 24 mol% to 52 mol% 5-methyl-1-nonene.
- a third embodiment which is the composition of any one of the first and the second embodiments, wherein the composition comprises a) from 76 mol% to 92 mol% C 10 monoolefins and b) from 1 mol% to 12 mol% C 14 monoolefins.
- a fourth embodiment which is the composition of any one of the first through the third embodiments further comprising from 0.1 mol% to 5 mol% C 12 monoolefins, the C 12 monoolefins comprising from 54 mol% to 74 mol% 1-dodecene.
- a fifth embodiment which is the composition of any one of the first through the fourth embodiments further comprising from 0.1 mol% to 5 mol% C 8 monoolefins, the C 8 monoolefins comprising at least 95 mol% 1-octene.
- a sixth embodiment which is the composition of any one of the first through the fifth embodiments further comprising from 0.05 mol% to 2 mol% C 16 monoolefins and/or C 18 monoolefins.
- a seventh embodiment which is the composition of any one of the first through the sixth embodiments further comprising from 0.2 mol% to 6 mol% acyclic saturated hydrocarbons.
- An eighth embodiment which is the composition of the seventh embodiment, wherein the acyclic saturated hydrocarbons comprise octane, decane, dodecane, tetradecane, or combinations thereof.
- a ninth embodiment which is the composition of any one of the first through the eighth embodiments, wherein the acyclic saturated hydrocarbons comprise a) from 10 mol% to 26 mol% octane, b) from 24 mol% to 48 mol% decane, c) from 22 mol% to 40 mol% dodecane, and d) from 7 mol% to 23 mol% tetradecane.
- a tenth embodiment which is the composition of any one of the first through the ninth embodiments further comprising from 1.9 mol% to 5.1 mol% cyclic saturated hydrocarbons.
- An eleventh embodiment which is the composition of the tenth embodiment, wherein the cyclic saturated hydrocarbon is methylcyclopentane, cyclohexane, methylcyclohexane, or combinations thereof.
- a twelfth embodiment which is the composition of any one of the first through the eleventh embodiments further comprising from 1 mol% to 3.4 mol% of a C 6 to C 12 aromatic hydrocarbon.
- a thirteenth embodiment which is the composition of the twelfth embodiment, wherein the aromatic hydrocarbon is benzene, toluene, ethylbenzene, xylene, mesitylene, hexamethylbenzene, or combinations thereof.
- a fourteenth embodiment which is the composition of any one of the first through the thirteenth embodiments further comprising from 0.4 mol% to 3 mol% of a C 4 to C 12 alcohol.
- a fifteenth embodiment which is the composition of the fourteenth embodiment, wherein the C 4 to C 12 alcohol is 1-hexanol, 2-hexanol, 3-hexanol, 2-ethyl-1-hexanol, 1-heptanol, 2-heptanol, 3-heptanol, 4-heptanol, 2-methyl-3-heptanol, 1-octanol, 2-octanol, 3-octanol, 4-octanol, 7-methyl-2-decanol, 1-decanol, 2-decanol, 3-decanol, 4-decanol, 5-decanol, 2-ethyl-1-decanol, or combinations thereof.
- the C 4 to C 12 alcohol is 1-hexanol, 2-hexanol, 3-hexanol, 2-ethyl-1-hexanol, 1-heptanol, 2-heptanol, 3-heptanol, 4-heptano
- a sixteenth embodiment which is a composition comprising at least 95 mol% C 10 monoolefins, the C 10 monoolefins comprising i) at least 3 mol% 2-butyl-1-hexene, ii) at least 10 mol% 3-propyl-1-heptene, iii) at least 7 mol% 4-ethyl-1-octene, and iv) at least 24 mol% 5-methyl-1-nonene.
- a seventeenth embodiment which is the composition of the sixteenth embodiment, wherein the composition comprises less than 3 mol% C 9- hydrocarbons, and less than 3 mol% C 11+ hydrocarbons.
- An eighteenth embodiment which is the composition of any one of the sixteenth and the seventeenth embodiments, wherein the C 10 monoolefins comprise i) from 3 mol% to 20 mol% 2-butyl-1-hexene, ii) from 10 mol% to 32 mol% 3-propyl-1-heptene, iii) from 7 mol% to 25 mol% 4-ethyl-1-octene, and iv) from 24 mol% to 52 mol% 5-methyl-1-nonene.
- a nineteenth embodiment which is the composition of any one of the sixteenth through the eighteenth embodiments, wherein a molar ratio of 5-methyl-1-nonene to 2-butyl-1-hexene is at least 2:1.
- a twentieth embodiment which is the composition of any one of the sixteenth through the nineteenth embodiments, wherein a molar ratio of 5-methyl-1-nonene to 3-propyl-1-heptene is at least 1.2:1.
- a twenty-first embodiment which is the composition of any one of the sixteenth through the twentieth embodiments, wherein a molar ratio of 5-methyl-1-nonene to 4-ethyl-1-octene is at least 1.6:1.
- a twenty-second embodiment which is the composition of any one of the sixteenth through the twenty-first embodiments, wherein the C 10 monoolefins comprise from 1 mol% to 16 mol% 4-decene and/or 5-decene.
- a twenty-third embodiment which is the composition of any one of the sixteenth through the twenty-second embodiments, wherein the C 10 monoolefins comprise from 0.5 mol% to 9 mol% 1-decene.
- a twenty-fourth embodiment which is a process comprising: a) contacting 1) ethylene, 2) a catalyst system comprising i) a chromium containing compound, ii) a heteroatomic ligand, and iii) an alkylaluminum compound, and 3) optionally a reaction system diluent; b) forming an oligomer product comprising 1-hexene and/or 1-octene in a reaction system; c) discharging a reaction system effluent from the reaction system; d) contacting the reaction system effluent with a catalyst system deactivating agent; and e) isolating a first composition comprising: (1) at least 76 mol% C 10 monoolefins, the C 10 monoolefins comprising (i) at least 3 mol% 2-butyl-1-hexene, (ii) at least 8 mol% 3-propyl-1-heptene, (iii) at least 6 mol% 4-
- a twenty-fifth embodiment which is the process of the twenty-fourth embodiment further comprising recovering a second composition comprising 95 mol% C 10 monoolefins from the first composition, the C 10 monoolefins comprising (i) at least 3 mol% 2-butyl-1-hexene, (ii) at least 10 mol% 3-propyl-1-heptene, (iii) at least 7 mol% 4-ethyl-1-octene, and (iv) at least 24 mol% 5-methyl-1-nonene.
- a twenty-sixth embodiment which is process of any one of the twenty-fourth and the twenty-fifth embodiments, wherein the catalyst system is prepared in a catalyst system solvent.
- a twenty-seventh embodiment which is the process of any one of the twenty-fourth through the twenty-sixth embodiments, wherein the reaction system effluent comprises the oligomer product comprising at least 60 mol% 1-hexene and/or 1-octene, the catalyst system, and the optional reaction system diluent.
- a twenty-eighth embodiment which is the process of any one of the twenty-fourth through the twenty-seventh embodiments, wherein the process further comprises isolating a stream comprising (a) at least 90 mol% 1-hexene, (b) at least 90 mol% 1-octene, or (c) at least 90 mol% 1-hexene and 1-octene.
- a twenty-ninth embodiment which is the process of any one of the twenty-fourth through the twenty-eighth embodiments, wherein the heteroatomic ligand is a pyrrole compound, a diphosphino aminyl compound, an N 2 -phosphinyl amidine compound, an N 2 -phosphinyl formamidine compound, an N 2 -phosphinyl guanidine compound, or combinations thereof.
- the heteroatomic ligand is a pyrrole compound, a diphosphino aminyl compound, an N 2 -phosphinyl amidine compound, an N 2 -phosphinyl formamidine compound, an N 2 -phosphinyl guanidine compound, or combinations thereof.
- a thirtieth embodiment which is the process of any one of the twenty-fourth through the twenty-ninth embodiments, wherein the catalyst system is selected from the group consisting of: a) a chromium containing compound, a pyrrole compound, an alkylaluminum compound, and optionally a halide containing compound; b) a chromium containing compound, a diphosphino aminyl compound, an alkylaluminum compound; c) a chromium containing compound complexed to a diphosphino aminyl compound, and an alkylaluminum compound; d) a chromium containing compound, an N 2 -phosphinyl amidine compound, and an alkylaluminum compound; e) a chromium containing compound complexed to an N 2 -phosphinyl amidine compound, and an alkylaluminum compound; f) a chromium containing compound, an N 2 -phos
- R l a numerical range with a lower limit, R l , and an upper limit, R u .
- R l any number falling within the range is specifically disclosed.
- any numerical range defined by two R numbers as defined in the above is also specifically disclosed.
- the present invention relates to the subject-matter defined in the following numbered statements.
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PCT/US2016/037581 WO2017011127A1 (en) | 2015-07-14 | 2016-06-15 | Olefin compositions |
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US20190263732A1 (en) | 2019-08-29 |
US20180127332A1 (en) | 2018-05-10 |
WO2017010998A1 (en) | 2017-01-19 |
EP3322680A1 (de) | 2018-05-23 |
US10435336B2 (en) | 2019-10-08 |
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